NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	936.49
Volume:	911.989
LogP:	3.854
LogD:	1.9
LogS:	-3.151
# Rotatable Bonds:	10
TPSA:	288.28
# H-Bond Aceptor:	20
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.091
Synthetic Accessibility Score:	7.277
Fsp3:	0.911
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.866
MDCK Permeability:	0.00027426728047430515
Pgp-inhibitor:	0.003
Pgp-substrate:	0.975
Human Intestinal Absorption (HIA):	0.346
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	92.14910888671875%
Volume Distribution (VD):	0.345
Pgp-substrate:	7.445794105529785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.169
CYP3A4-substrate:	0.021

ADMET: Excretion

Clearance (CL):	0.806
Half-life (T1/2):	0.553

ADMET: Toxicity

hERG Blockers:	0.97
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.203
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.523
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.087

Download Data

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

Natural Product: NPC477349

Natural Product ID:	NPC477349
*Common Name:**	Tyrianthin 8
IUPAC Name:	[(1S,3R,4R,5R,6R,8S,10R,11R,12R,13R,15R,29R,30R,31R,33R)-4,5,11,12-tetrahydroxy-6-(hydroxymethyl)-13,31-dimethyl-27-oxo-17-pentyl-30-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,7,9,14,16,28,32-heptaoxatetracyclo[27.3.1.03,8.010,15]tritriacontan-33-yl] (E)-2-methylbut-2-enoate
Synonyms:	Tyrianthin 8
Standard InCHIKey:	MDEMDKARDFUEHH-PSTHPRIPSA-N
Standard InCHI:	InChI=1S/C45H76O20/c1-7-9-15-18-26-19-16-13-11-10-12-14-17-20-28(47)61-39-36(63-42-35(54)32(51)29(48)23(4)56-42)25(6)58-45(40(39)62-41(55)22(3)8-2)65-38-34(53)31(50)27(21-46)60-44(38)64-37-33(52)30(49)24(5)57-43(37)59-26/h8,23-27,29-40,42-46,48-54H,7,9-21H2,1-6H3/b22-8+/t23-,24-,25-,26?,27-,29+,30+,31+,32-,33-,34-,35-,36-,37-,38-,39-,40-,42-,43+,44+,45+/m1/s1
SMILES:	CCCCCC1CCCCCCCCCC(=O)O[C@@H]2[C@@H]([C@H](O[C@H]([C@@H]2OC(=O)/C(=C/C)/C)O[C@@H]3[C@@H]([C@H]([C@H](O[C@H]3O[C@@H]4[C@@H]([C@H]([C@H](O[C@H]4O1)C)O)O)CO)O)O)C)O[C@@H]5[C@@H]([C@@H]([C@H]([C@H](O5)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44579632
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO4441	Ipomoea tyrianthina	Species	Convolvulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17309299]
NPO4441	Ipomoea tyrianthina	Species	Convolvulaceae	Eukaryota	Roots	states of Puebla, Morelos, and Distrito Federal, Mexico	2000-2005	PMID[18826278]
NPO4441	Ipomoea tyrianthina	Species	Convolvulaceae	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
MIC	1
Others	1

Activity Type	# Activity
Cell Line	3
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.2	ug/ml	PMID[18826278]
NPT382	Cell Line	OVCAR-5	Homo sapiens	ED50	>	5	ug/ml	PMID[18826278]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	5	ug/ml	PMID[18826278]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	25	ug/ml	PMID[18826278]
NPT2	Others	Unspecified		ED50	>	5	ug/ml	PMID[18826278]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	70	%	PMID[18826278]

☑ 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 NPC477349 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	276
0.1-0.2	2348
0.2-0.3	6752
0.3-0.4	14119
0.4-0.5	10089
0.5-0.6	6395
0.6-0.7	2116
0.7-0.8	539
0.8-0.85	41
0.85-0.9	2
0.9-0.95	2
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC163409
0.977	High Similarity	NPC44682
0.977	High Similarity	NPC238264
0.977	High Similarity	NPC477345
0.977	High Similarity	NPC477348
0.9551	High Similarity	NPC475540
0.9551	High Similarity	NPC473765
0.9551	High Similarity	NPC475525
0.9551	High Similarity	NPC476066
0.9551	High Similarity	NPC473605
0.9551	High Similarity	NPC475375
0.9551	High Similarity	NPC475241
0.9551	High Similarity	NPC475164
0.9551	High Similarity	NPC475593
0.8736	High Similarity	NPC288471
0.8478	Intermediate Similarity	NPC110072
0.8261	Intermediate Similarity	NPC285588
0.8235	Intermediate Similarity	NPC477350
0.8161	Intermediate Similarity	NPC85759
0.8161	Intermediate Similarity	NPC22742
0.8161	Intermediate Similarity	NPC146992
0.8161	Intermediate Similarity	NPC477344
0.8161	Intermediate Similarity	NPC158302
0.8161	Intermediate Similarity	NPC477346
0.8161	Intermediate Similarity	NPC294748
0.814	Intermediate Similarity	NPC476782
0.814	Intermediate Similarity	NPC476783
0.814	Intermediate Similarity	NPC216883
0.814	Intermediate Similarity	NPC476781
0.8068	Intermediate Similarity	NPC267592
0.8046	Intermediate Similarity	NPC477328
0.8046	Intermediate Similarity	NPC477330
0.8046	Intermediate Similarity	NPC113745
0.8046	Intermediate Similarity	NPC477323
0.8046	Intermediate Similarity	NPC477326
0.8046	Intermediate Similarity	NPC477320
0.8046	Intermediate Similarity	NPC477329
0.8046	Intermediate Similarity	NPC109887
0.8046	Intermediate Similarity	NPC281563
0.8046	Intermediate Similarity	NPC475425
0.8046	Intermediate Similarity	NPC477325
0.8046	Intermediate Similarity	NPC146380
0.8	Intermediate Similarity	NPC320089
0.798	Intermediate Similarity	NPC154132
0.798	Intermediate Similarity	NPC475655
0.798	Intermediate Similarity	NPC57586
0.798	Intermediate Similarity	NPC475157
0.798	Intermediate Similarity	NPC471637
0.798	Intermediate Similarity	NPC2313
0.7978	Intermediate Similarity	NPC169345
0.7978	Intermediate Similarity	NPC173328
0.7978	Intermediate Similarity	NPC472201
0.7978	Intermediate Similarity	NPC477317
0.7978	Intermediate Similarity	NPC472202
0.7978	Intermediate Similarity	NPC472200
0.7978	Intermediate Similarity	NPC89843
0.7978	Intermediate Similarity	NPC472204
0.7978	Intermediate Similarity	NPC472203
0.7978	Intermediate Similarity	NPC290012
0.7978	Intermediate Similarity	NPC259294
0.7978	Intermediate Similarity	NPC123204
0.7978	Intermediate Similarity	NPC184915
0.7978	Intermediate Similarity	NPC27289
0.7978	Intermediate Similarity	NPC477347
0.7978	Intermediate Similarity	NPC269318
0.7978	Intermediate Similarity	NPC44782
0.7978	Intermediate Similarity	NPC477319
0.7978	Intermediate Similarity	NPC475327
0.7978	Intermediate Similarity	NPC477331
0.7978	Intermediate Similarity	NPC115013
0.7978	Intermediate Similarity	NPC186992
0.7978	Intermediate Similarity	NPC475270
0.7978	Intermediate Similarity	NPC475667
0.7978	Intermediate Similarity	NPC183888
0.7978	Intermediate Similarity	NPC238056
0.7978	Intermediate Similarity	NPC224953
0.7978	Intermediate Similarity	NPC143421
0.7978	Intermediate Similarity	NPC307400
0.7978	Intermediate Similarity	NPC476087
0.7978	Intermediate Similarity	NPC472205
0.7978	Intermediate Similarity	NPC119583
0.7978	Intermediate Similarity	NPC126685
0.7978	Intermediate Similarity	NPC297768
0.7978	Intermediate Similarity	NPC477318
0.7882	Intermediate Similarity	NPC9763
0.7882	Intermediate Similarity	NPC225748
0.7882	Intermediate Similarity	NPC39266
0.7882	Intermediate Similarity	NPC206823
0.7882	Intermediate Similarity	NPC163812
0.7882	Intermediate Similarity	NPC169085
0.7849	Intermediate Similarity	NPC475186
0.7849	Intermediate Similarity	NPC118077
0.7802	Intermediate Similarity	NPC472352
0.7802	Intermediate Similarity	NPC156089
0.7802	Intermediate Similarity	NPC470313
0.7802	Intermediate Similarity	NPC60849
0.7802	Intermediate Similarity	NPC473500
0.7802	Intermediate Similarity	NPC477332
0.7802	Intermediate Similarity	NPC38295
0.7755	Intermediate Similarity	NPC143446
0.7732	Intermediate Similarity	NPC159698
0.7692	Intermediate Similarity	NPC193765
0.767	Intermediate Similarity	NPC476738
0.767	Intermediate Similarity	NPC315070
0.767	Intermediate Similarity	NPC476740
0.7667	Intermediate Similarity	NPC163362
0.7667	Intermediate Similarity	NPC127295
0.7653	Intermediate Similarity	NPC469543
0.7647	Intermediate Similarity	NPC309398
0.7647	Intermediate Similarity	NPC52268
0.7647	Intermediate Similarity	NPC474581
0.7647	Intermediate Similarity	NPC473816
0.7647	Intermediate Similarity	NPC475367
0.7647	Intermediate Similarity	NPC197736
0.7647	Intermediate Similarity	NPC53760
0.7629	Intermediate Similarity	NPC238090
0.7629	Intermediate Similarity	NPC472195
0.7629	Intermediate Similarity	NPC472196
0.7582	Intermediate Similarity	NPC469469
0.7582	Intermediate Similarity	NPC236649
0.7582	Intermediate Similarity	NPC21693
0.7553	Intermediate Similarity	NPC47937
0.7551	Intermediate Similarity	NPC294293
0.7529	Intermediate Similarity	NPC211428
0.7529	Intermediate Similarity	NPC241265
0.7529	Intermediate Similarity	NPC285003
0.7524	Intermediate Similarity	NPC177524
0.7524	Intermediate Similarity	NPC219900
0.7524	Intermediate Similarity	NPC392
0.7451	Intermediate Similarity	NPC476611
0.7449	Intermediate Similarity	NPC473520
0.7449	Intermediate Similarity	NPC473561
0.7449	Intermediate Similarity	NPC475173
0.7449	Intermediate Similarity	NPC473723
0.7449	Intermediate Similarity	NPC473663
0.7447	Intermediate Similarity	NPC329838
0.7447	Intermediate Similarity	NPC120398
0.7447	Intermediate Similarity	NPC470124
0.7447	Intermediate Similarity	NPC477013
0.7447	Intermediate Similarity	NPC182383
0.7447	Intermediate Similarity	NPC477014
0.7447	Intermediate Similarity	NPC329615
0.7447	Intermediate Similarity	NPC471567
0.7423	Intermediate Similarity	NPC473904
0.7423	Intermediate Similarity	NPC473311
0.7412	Intermediate Similarity	NPC67099
0.7412	Intermediate Similarity	NPC50228
0.7412	Intermediate Similarity	NPC97736
0.7412	Intermediate Similarity	NPC250619
0.7411	Intermediate Similarity	NPC476150
0.7411	Intermediate Similarity	NPC476127
0.74	Intermediate Similarity	NPC306041
0.7396	Intermediate Similarity	NPC20339
0.7396	Intermediate Similarity	NPC320458
0.7396	Intermediate Similarity	NPC280621
0.7396	Intermediate Similarity	NPC40376
0.7396	Intermediate Similarity	NPC89001
0.7396	Intermediate Similarity	NPC48338
0.7396	Intermediate Similarity	NPC233551
0.7396	Intermediate Similarity	NPC473905
0.7396	Intermediate Similarity	NPC21208
0.7391	Intermediate Similarity	NPC297950
0.7368	Intermediate Similarity	NPC208473
0.7368	Intermediate Similarity	NPC477015
0.7347	Intermediate Similarity	NPC473707
0.7347	Intermediate Similarity	NPC472197
0.734	Intermediate Similarity	NPC163093
0.734	Intermediate Similarity	NPC156804
0.7328	Intermediate Similarity	NPC470516
0.732	Intermediate Similarity	NPC477017
0.732	Intermediate Similarity	NPC477016
0.732	Intermediate Similarity	NPC139418
0.7315	Intermediate Similarity	NPC126897
0.7315	Intermediate Similarity	NPC297945
0.7297	Intermediate Similarity	NPC474483
0.7294	Intermediate Similarity	NPC206601
0.7292	Intermediate Similarity	NPC20533
0.7292	Intermediate Similarity	NPC476583
0.7292	Intermediate Similarity	NPC473995
0.7292	Intermediate Similarity	NPC258068
0.7292	Intermediate Similarity	NPC125142
0.7292	Intermediate Similarity	NPC178215
0.7273	Intermediate Similarity	NPC308096
0.7273	Intermediate Similarity	NPC291228
0.7265	Intermediate Similarity	NPC87153
0.7265	Intermediate Similarity	NPC472269
0.7265	Intermediate Similarity	NPC45606
0.7265	Intermediate Similarity	NPC472270
0.7265	Intermediate Similarity	NPC112492
0.7265	Intermediate Similarity	NPC23020
0.7265	Intermediate Similarity	NPC220838
0.7265	Intermediate Similarity	NPC162925
0.7265	Intermediate Similarity	NPC472268
0.7263	Intermediate Similarity	NPC322529
0.7255	Intermediate Similarity	NPC198422
0.7255	Intermediate Similarity	NPC40182
0.7255	Intermediate Similarity	NPC472015
0.7245	Intermediate Similarity	NPC239517
0.7245	Intermediate Similarity	NPC470573
0.7245	Intermediate Similarity	NPC120021

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 NPC477349 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	2709
0.2-0.3	3914
0.3-0.4	1501
0.4-0.5	531
0.5-0.6	168
0.6-0.7	32
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
0.7524	Intermediate Similarity	NPD6686	Approved
0.7315	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD46	Approved
0.7245	Intermediate Similarity	NPD6698	Approved
0.7087	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8515	Approved
0.7043	Intermediate Similarity	NPD8516	Approved
0.7043	Intermediate Similarity	NPD8517	Approved
0.7027	Intermediate Similarity	NPD8133	Approved
0.6989	Remote Similarity	NPD7329	Approved
0.6897	Remote Similarity	NPD8513	Phase 3
0.6639	Remote Similarity	NPD7829	Approved
0.6639	Remote Similarity	NPD7830	Approved
0.6588	Remote Similarity	NPD6123	Approved
0.6569	Remote Similarity	NPD7838	Discovery
0.6529	Remote Similarity	NPD7507	Approved
0.6525	Remote Similarity	NPD8377	Approved
0.6525	Remote Similarity	NPD8294	Approved
0.65	Remote Similarity	NPD8328	Phase 3
0.6486	Remote Similarity	NPD6412	Phase 2
0.6471	Remote Similarity	NPD8380	Approved
0.6471	Remote Similarity	NPD8379	Approved
0.6471	Remote Similarity	NPD8296	Approved
0.6471	Remote Similarity	NPD8335	Approved
0.6471	Remote Similarity	NPD8378	Approved
0.6371	Remote Similarity	NPD7319	Approved
0.6346	Remote Similarity	NPD7983	Approved
0.6333	Remote Similarity	NPD8033	Approved
0.6228	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7328	Approved
0.6218	Remote Similarity	NPD7327	Approved
0.621	Remote Similarity	NPD8448	Approved
0.6198	Remote Similarity	NPD8444	Approved
0.6198	Remote Similarity	NPD7503	Approved
0.6195	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8390	Approved
0.619	Remote Similarity	NPD8392	Approved
0.619	Remote Similarity	NPD8391	Approved
0.617	Remote Similarity	NPD3181	Approved
0.6167	Remote Similarity	NPD7516	Approved
0.6129	Remote Similarity	NPD8451	Approved
0.6098	Remote Similarity	NPD7642	Approved
0.6083	Remote Similarity	NPD7641	Discontinued
0.608	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD897	Approved
0.5978	Remote Similarity	NPD898	Approved
0.5978	Remote Similarity	NPD896	Approved
0.5963	Remote Similarity	NPD7839	Suspended
0.592	Remote Similarity	NPD8340	Approved
0.592	Remote Similarity	NPD8342	Approved
0.592	Remote Similarity	NPD8299	Approved
0.592	Remote Similarity	NPD8341	Approved
0.5897	Remote Similarity	NPD6371	Approved
0.5882	Remote Similarity	NPD3730	Approved
0.5882	Remote Similarity	NPD3728	Approved
0.5882	Remote Similarity	NPD7346	Approved
0.5877	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD8082	Approved
0.5841	Remote Similarity	NPD8084	Approved
0.5841	Remote Similarity	NPD8139	Approved
0.5841	Remote Similarity	NPD8085	Approved
0.5841	Remote Similarity	NPD8138	Approved
0.5841	Remote Similarity	NPD8083	Approved
0.5841	Remote Similarity	NPD8086	Approved
0.5826	Remote Similarity	NPD8393	Approved
0.5825	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD8276	Approved
0.5789	Remote Similarity	NPD8275	Approved
0.5781	Remote Similarity	NPD7736	Approved
0.5765	Remote Similarity	NPD888	Phase 3
0.5765	Remote Similarity	NPD892	Phase 3
0.5765	Remote Similarity	NPD893	Approved
0.5765	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD891	Phase 3
0.576	Remote Similarity	NPD8080	Discontinued
0.5752	Remote Similarity	NPD5344	Discontinued
0.5739	Remote Similarity	NPD8081	Approved
0.5738	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7638	Approved
0.5702	Remote Similarity	NPD7139	Approved
0.5702	Remote Similarity	NPD7140	Approved
0.5702	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.568	Remote Similarity	NPD8267	Approved
0.568	Remote Similarity	NPD8266	Approved
0.568	Remote Similarity	NPD8269	Approved
0.568	Remote Similarity	NPD8268	Approved
0.5678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6053	Discontinued
0.5667	Remote Similarity	NPD6429	Approved
0.5667	Remote Similarity	NPD6430	Approved
0.5664	Remote Similarity	NPD7639	Approved
0.5664	Remote Similarity	NPD7640	Approved
0.5647	Remote Similarity	NPD2269	Approved
0.5641	Remote Similarity	NPD8307	Discontinued
0.5641	Remote Similarity	NPD8140	Approved
0.561	Remote Similarity	NPD7115	Discovery

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