NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1038.56
Volume:	1021.969
LogP:	4.076
LogD:	2.385
LogS:	-3.632
# Rotatable Bonds:	30
TPSA:	325.58
# H-Bond Aceptor:	22
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.031
Synthetic Accessibility Score:	6.302
Fsp3:	0.9
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.953
MDCK Permeability:	0.00022187053400557488
Pgp-inhibitor:	0.903
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.902
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.862

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	96.78185272216797%
Volume Distribution (VD):	0.443
Pgp-substrate:	7.517622470855713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.159
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	0.76
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.623
Human Hepatotoxicity (H-HT):	0.829
Drug-inuced Liver Injury (DILI):	0.736
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.431
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.121

Download Data

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

Natural Product: NPC477348

Natural Product ID:	NPC477348
*Common Name:**	Thyrianthinic acid II
IUPAC Name:	(11R)-11-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R,5R,6S)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-methyl-5-[(E)-2-methylbut-2-enoyl]oxyoxan-2-yl]oxy-4-hydroxy-6-methyl-3-(2-methylbutanoyloxy)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxyhexadecanoic acid
Synonyms:	Thyrianthinic acid II
Standard InCHIKey:	JOEODRFAFPATFF-ZPDOANOZSA-N
Standard InCHI:	InChI=1S/C50H86O22/c1-9-12-18-21-30(22-19-16-14-13-15-17-20-23-32(52)53)66-48-42(35(56)33(54)27(6)63-48)72-50-43(36(57)34(55)31(24-51)67-50)71-49-44(69-46(62)26(5)11-3)39(60)41(29(8)65-49)70-47-38(59)37(58)40(28(7)64-47)68-45(61)25(4)10-2/h10,26-31,33-44,47-51,54-60H,9,11-24H2,1-8H3,(H,52,53)/b25-10+/t26?,27-,28-,29+,30-,31-,33-,34-,35+,36+,37-,38-,39-,40-,41+,42-,43-,44-,47+,48+,49+,50+/m1/s1
SMILES:	CCCCC[C@H](CCCCCCCCCC(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C)OC(=O)/C(=C/C)/C)O)O)O)OC(=O)C(C)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	25135430
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	=	2.8	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 NPC477348 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	262
0.1-0.2	2172
0.2-0.3	6369
0.3-0.4	13568
0.4-0.5	10014
0.5-0.6	6984
0.6-0.7	2577
0.7-0.8	662
0.8-0.85	68
0.85-0.9	0
0.9-0.95	6
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC238264
1.0	High Similarity	NPC477345
0.9775	High Similarity	NPC475540
0.9775	High Similarity	NPC473765
0.9775	High Similarity	NPC475375
0.9775	High Similarity	NPC473605
0.9775	High Similarity	NPC476066
0.9775	High Similarity	NPC475593
0.9775	High Similarity	NPC475241
0.9775	High Similarity	NPC475164
0.9775	High Similarity	NPC475525
0.977	High Similarity	NPC477349
0.9551	High Similarity	NPC44682
0.9551	High Similarity	NPC163409
0.8539	High Similarity	NPC288471
0.8391	Intermediate Similarity	NPC294748
0.8391	Intermediate Similarity	NPC85759
0.8391	Intermediate Similarity	NPC477344
0.8391	Intermediate Similarity	NPC158302
0.8391	Intermediate Similarity	NPC146992
0.8391	Intermediate Similarity	NPC477346
0.8391	Intermediate Similarity	NPC22742
0.8298	Intermediate Similarity	NPC110072
0.8202	Intermediate Similarity	NPC475270
0.8202	Intermediate Similarity	NPC477319
0.8202	Intermediate Similarity	NPC184915
0.8202	Intermediate Similarity	NPC27289
0.8202	Intermediate Similarity	NPC169345
0.8202	Intermediate Similarity	NPC472202
0.8202	Intermediate Similarity	NPC259294
0.8202	Intermediate Similarity	NPC475327
0.8202	Intermediate Similarity	NPC224953
0.8202	Intermediate Similarity	NPC173328
0.8202	Intermediate Similarity	NPC269318
0.8202	Intermediate Similarity	NPC115013
0.8202	Intermediate Similarity	NPC475667
0.8202	Intermediate Similarity	NPC183888
0.8202	Intermediate Similarity	NPC123204
0.8202	Intermediate Similarity	NPC472201
0.8202	Intermediate Similarity	NPC477331
0.8202	Intermediate Similarity	NPC477318
0.8202	Intermediate Similarity	NPC472203
0.8202	Intermediate Similarity	NPC143421
0.8202	Intermediate Similarity	NPC297768
0.8202	Intermediate Similarity	NPC89843
0.8202	Intermediate Similarity	NPC307400
0.8202	Intermediate Similarity	NPC472204
0.8202	Intermediate Similarity	NPC126685
0.8202	Intermediate Similarity	NPC476087
0.8202	Intermediate Similarity	NPC44782
0.8202	Intermediate Similarity	NPC119583
0.8202	Intermediate Similarity	NPC472205
0.8202	Intermediate Similarity	NPC477347
0.8202	Intermediate Similarity	NPC186992
0.8202	Intermediate Similarity	NPC238056
0.8202	Intermediate Similarity	NPC472200
0.8202	Intermediate Similarity	NPC290012
0.8202	Intermediate Similarity	NPC477317
0.8182	Intermediate Similarity	NPC57586
0.8182	Intermediate Similarity	NPC471637
0.8182	Intermediate Similarity	NPC475157
0.8182	Intermediate Similarity	NPC154132
0.8182	Intermediate Similarity	NPC2313
0.8182	Intermediate Similarity	NPC475655
0.809	Intermediate Similarity	NPC267592
0.8085	Intermediate Similarity	NPC285588
0.8046	Intermediate Similarity	NPC477350
0.8022	Intermediate Similarity	NPC60849
0.8022	Intermediate Similarity	NPC477332
0.8022	Intermediate Similarity	NPC472352
0.8021	Intermediate Similarity	NPC320089
0.7955	Intermediate Similarity	NPC476783
0.7955	Intermediate Similarity	NPC216883
0.7955	Intermediate Similarity	NPC476782
0.7955	Intermediate Similarity	NPC476781
0.7938	Intermediate Similarity	NPC159698
0.7865	Intermediate Similarity	NPC281563
0.7865	Intermediate Similarity	NPC109887
0.7865	Intermediate Similarity	NPC477326
0.7865	Intermediate Similarity	NPC477329
0.7865	Intermediate Similarity	NPC477330
0.7865	Intermediate Similarity	NPC146380
0.7865	Intermediate Similarity	NPC113745
0.7865	Intermediate Similarity	NPC477323
0.7865	Intermediate Similarity	NPC477320
0.7865	Intermediate Similarity	NPC477325
0.7865	Intermediate Similarity	NPC477328
0.7865	Intermediate Similarity	NPC475425
0.7864	Intermediate Similarity	NPC476738
0.7864	Intermediate Similarity	NPC315070
0.7864	Intermediate Similarity	NPC476740
0.7857	Intermediate Similarity	NPC469543
0.7843	Intermediate Similarity	NPC197736
0.7835	Intermediate Similarity	NPC472196
0.7835	Intermediate Similarity	NPC238090
0.7835	Intermediate Similarity	NPC472195
0.7778	Intermediate Similarity	NPC143446
0.7714	Intermediate Similarity	NPC193765
0.7714	Intermediate Similarity	NPC392
0.7714	Intermediate Similarity	NPC219900
0.7714	Intermediate Similarity	NPC177524
0.7701	Intermediate Similarity	NPC9763
0.7701	Intermediate Similarity	NPC39266
0.7701	Intermediate Similarity	NPC169085
0.7701	Intermediate Similarity	NPC206823
0.7701	Intermediate Similarity	NPC163812
0.7701	Intermediate Similarity	NPC225748
0.7684	Intermediate Similarity	NPC475186
0.7684	Intermediate Similarity	NPC118077
0.767	Intermediate Similarity	NPC474581
0.767	Intermediate Similarity	NPC309398
0.767	Intermediate Similarity	NPC473816
0.767	Intermediate Similarity	NPC475367
0.7647	Intermediate Similarity	NPC476611
0.7634	Intermediate Similarity	NPC38295
0.7634	Intermediate Similarity	NPC470313
0.7634	Intermediate Similarity	NPC473500
0.7634	Intermediate Similarity	NPC156089
0.76	Intermediate Similarity	NPC306041
0.7589	Intermediate Similarity	NPC476127
0.7589	Intermediate Similarity	NPC476150
0.7576	Intermediate Similarity	NPC294293
0.7565	Intermediate Similarity	NPC297950
0.7551	Intermediate Similarity	NPC472197
0.75	Intermediate Similarity	NPC470516
0.75	Intermediate Similarity	NPC127295
0.75	Intermediate Similarity	NPC163362
0.75	Intermediate Similarity	NPC297945
0.75	Intermediate Similarity	NPC126897
0.7477	Intermediate Similarity	NPC474483
0.7471	Intermediate Similarity	NPC53760
0.7471	Intermediate Similarity	NPC52268
0.7451	Intermediate Similarity	NPC40182
0.7451	Intermediate Similarity	NPC198422
0.7451	Intermediate Similarity	NPC472015
0.7449	Intermediate Similarity	NPC470573
0.7449	Intermediate Similarity	NPC231710
0.7449	Intermediate Similarity	NPC303451
0.7449	Intermediate Similarity	NPC270908
0.7449	Intermediate Similarity	NPC120021
0.7449	Intermediate Similarity	NPC65665
0.7449	Intermediate Similarity	NPC6414
0.7449	Intermediate Similarity	NPC216826
0.7436	Intermediate Similarity	NPC23020
0.7436	Intermediate Similarity	NPC112492
0.7436	Intermediate Similarity	NPC220838
0.7436	Intermediate Similarity	NPC472268
0.7436	Intermediate Similarity	NPC472270
0.7436	Intermediate Similarity	NPC472269
0.7436	Intermediate Similarity	NPC45606
0.7426	Intermediate Similarity	NPC54731
0.7419	Intermediate Similarity	NPC469469
0.7419	Intermediate Similarity	NPC21693
0.7419	Intermediate Similarity	NPC236649
0.7411	Intermediate Similarity	NPC471548
0.7411	Intermediate Similarity	NPC470515
0.7404	Intermediate Similarity	NPC222062
0.7404	Intermediate Similarity	NPC201191
0.74	Intermediate Similarity	NPC472198
0.7396	Intermediate Similarity	NPC47937
0.7374	Intermediate Similarity	NPC472125
0.7374	Intermediate Similarity	NPC472199
0.7374	Intermediate Similarity	NPC477749
0.7374	Intermediate Similarity	NPC472124
0.7374	Intermediate Similarity	NPC472126
0.7368	Intermediate Similarity	NPC476204
0.7368	Intermediate Similarity	NPC170084
0.7368	Intermediate Similarity	NPC266718
0.7356	Intermediate Similarity	NPC211428
0.7356	Intermediate Similarity	NPC241265
0.7356	Intermediate Similarity	NPC285003
0.7353	Intermediate Similarity	NPC278506
0.7353	Intermediate Similarity	NPC476612
0.7353	Intermediate Similarity	NPC476613
0.7353	Intermediate Similarity	NPC475332
0.7345	Intermediate Similarity	NPC470915
0.7345	Intermediate Similarity	NPC470911
0.7345	Intermediate Similarity	NPC470517
0.7333	Intermediate Similarity	NPC118761
0.7333	Intermediate Similarity	NPC197541
0.7333	Intermediate Similarity	NPC267869
0.7333	Intermediate Similarity	NPC284929
0.7333	Intermediate Similarity	NPC234304
0.7321	Intermediate Similarity	NPC473405
0.732	Intermediate Similarity	NPC125142
0.7315	Intermediate Similarity	NPC313668
0.7315	Intermediate Similarity	NPC315836
0.7311	Intermediate Similarity	NPC290276
0.7311	Intermediate Similarity	NPC198918
0.7311	Intermediate Similarity	NPC204214
0.7311	Intermediate Similarity	NPC92283
0.7311	Intermediate Similarity	NPC124878
0.7311	Intermediate Similarity	NPC147032
0.7311	Intermediate Similarity	NPC10121
0.7311	Intermediate Similarity	NPC63404
0.7311	Intermediate Similarity	NPC300655
0.7311	Intermediate Similarity	NPC222951
0.7311	Intermediate Similarity	NPC10883
0.7311	Intermediate Similarity	NPC43589
0.7311	Intermediate Similarity	NPC231888

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 NPC477348 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	2585
0.2-0.3	3892
0.3-0.4	1595
0.4-0.5	568
0.5-0.6	191
0.6-0.7	40
0.7-0.8	9
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
0.7714	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD46	Approved
0.7449	Intermediate Similarity	NPD6698	Approved
0.7282	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD8516	Approved
0.7217	Intermediate Similarity	NPD8517	Approved
0.7217	Intermediate Similarity	NPD8515	Approved
0.7207	Intermediate Similarity	NPD8133	Approved
0.7069	Intermediate Similarity	NPD8513	Phase 3
0.6842	Remote Similarity	NPD7329	Approved
0.6807	Remote Similarity	NPD7830	Approved
0.6807	Remote Similarity	NPD7829	Approved
0.6765	Remote Similarity	NPD7838	Discovery
0.6695	Remote Similarity	NPD8377	Approved
0.6695	Remote Similarity	NPD8294	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD8378	Approved
0.6639	Remote Similarity	NPD8296	Approved
0.6639	Remote Similarity	NPD8335	Approved
0.6639	Remote Similarity	NPD8380	Approved
0.6639	Remote Similarity	NPD8379	Approved
0.6538	Remote Similarity	NPD7983	Approved
0.6532	Remote Similarity	NPD7319	Approved
0.65	Remote Similarity	NPD8033	Approved
0.6437	Remote Similarity	NPD6123	Approved
0.6404	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7328	Approved
0.6387	Remote Similarity	NPD7327	Approved
0.6372	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8448	Approved
0.6364	Remote Similarity	NPD8444	Approved
0.6364	Remote Similarity	NPD7503	Approved
0.6349	Remote Similarity	NPD8392	Approved
0.6349	Remote Similarity	NPD8390	Approved
0.6349	Remote Similarity	NPD8391	Approved
0.6333	Remote Similarity	NPD7516	Approved
0.629	Remote Similarity	NPD8451	Approved
0.626	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD7641	Discontinued
0.624	Remote Similarity	NPD8074	Phase 3
0.6167	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7839	Suspended
0.608	Remote Similarity	NPD8340	Approved
0.608	Remote Similarity	NPD8342	Approved
0.608	Remote Similarity	NPD8341	Approved
0.608	Remote Similarity	NPD8299	Approved
0.6068	Remote Similarity	NPD6371	Approved
0.6053	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3181	Approved
0.6018	Remote Similarity	NPD8138	Approved
0.6018	Remote Similarity	NPD8082	Approved
0.6018	Remote Similarity	NPD8086	Approved
0.6018	Remote Similarity	NPD8139	Approved
0.6018	Remote Similarity	NPD8083	Approved
0.6018	Remote Similarity	NPD8084	Approved
0.6018	Remote Similarity	NPD8085	Approved
0.6	Remote Similarity	NPD8393	Approved
0.5965	Remote Similarity	NPD8275	Approved
0.5965	Remote Similarity	NPD8276	Approved
0.594	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7736	Approved
0.5929	Remote Similarity	NPD5344	Discontinued
0.592	Remote Similarity	NPD8080	Discontinued
0.5913	Remote Similarity	NPD8081	Approved
0.5902	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7638	Approved
0.5865	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD898	Approved
0.5851	Remote Similarity	NPD897	Approved
0.5851	Remote Similarity	NPD896	Approved
0.5847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7639	Approved
0.5841	Remote Similarity	NPD7640	Approved
0.584	Remote Similarity	NPD8266	Approved
0.584	Remote Similarity	NPD8267	Approved
0.584	Remote Similarity	NPD8269	Approved
0.584	Remote Similarity	NPD8268	Approved
0.5833	Remote Similarity	NPD6053	Discontinued
0.5812	Remote Similarity	NPD8140	Approved
0.5812	Remote Similarity	NPD8307	Discontinued
0.5772	Remote Similarity	NPD7115	Discovery
0.5769	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD3669	Approved
0.5763	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD4225	Approved
0.5747	Remote Similarity	NPD3728	Approved
0.5747	Remote Similarity	NPD3730	Approved
0.5747	Remote Similarity	NPD7346	Approved
0.5746	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD8293	Discontinued
0.5727	Remote Similarity	NPD5778	Approved
0.5727	Remote Similarity	NPD5779	Approved
0.5714	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8306	Approved
0.5714	Remote Similarity	NPD8305	Approved
0.5699	Remote Similarity	NPD7909	Approved
0.5692	Remote Similarity	NPD8337	Approved
0.5692	Remote Similarity	NPD8336	Approved
0.5688	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD8415	Approved
0.567	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD6370	Approved
0.5667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8087	Discontinued
0.566	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD892	Phase 3
0.5632	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD888	Phase 3
0.5632	Remote Similarity	NPD893	Approved
0.5632	Remote Similarity	NPD891	Phase 3
0.5619	Remote Similarity	NPD7154	Phase 3
0.5603	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD7139	Approved
0.5603	Remote Similarity	NPD7140	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