NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	910.48
Volume:	880.033
LogP:	3.766
LogD:	1.985
LogS:	-3.208
# 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:	0.114
Synthetic Accessibility Score:	7.159
Fsp3:	0.953
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:	-5.857
MDCK Permeability:	0.00024437002139166
Pgp-inhibitor:	0.0
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.498
20% Bioavailability (F20%):	0.315
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	89.2535629272461%
Volume Distribution (VD):	0.316
Pgp-substrate:	6.0125861167907715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	0.809
Half-life (T1/2):	0.568

ADMET: Toxicity

hERG Blockers:	0.97
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.233
Rat Oral Acute Toxicity:	0.354
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.387
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC477350

Natural Product ID:	NPC477350
*Common Name:**	Tyrianthin 9
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] propanoate
Synonyms:	Tyrianthin 9
Standard InCHIKey:	PVATZCKYGRERLI-XIZJVXPQSA-N
Standard InCHI:	InChI=1S/C43H74O20/c1-6-8-14-17-24-18-15-12-10-9-11-13-16-19-27(46)60-38-35(61-40-34(53)31(50)28(47)21(3)54-40)23(5)56-43(39(38)59-26(45)7-2)63-37-33(52)30(49)25(20-44)58-42(37)62-36-32(51)29(48)22(4)55-41(36)57-24/h21-25,28-44,47-53H,6-20H2,1-5H3/t21-,22-,23-,24?,25-,28+,29+,30+,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41+,42+,43+/m1/s1
SMILES:	CCCCCC1CCCCCCCCCC(=O)O[C@@H]2[C@@H]([C@H](O[C@H]([C@@H]2OC(=O)CC)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:	44579633
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	=	2.5	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 NPC477350 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	768
0.1-0.2	4808
0.2-0.3	14280
0.3-0.4	11383
0.4-0.5	6609
0.5-0.6	3459
0.6-0.7	1211
0.7-0.8	73
0.8-0.85	14
0.85-0.9	15
0.9-0.95	63
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC476781
0.9859	High Similarity	NPC476783
0.9859	High Similarity	NPC216883
0.9859	High Similarity	NPC476782
0.9722	High Similarity	NPC146380
0.9722	High Similarity	NPC477329
0.9722	High Similarity	NPC113745
0.9722	High Similarity	NPC477323
0.9722	High Similarity	NPC477320
0.9722	High Similarity	NPC477330
0.9722	High Similarity	NPC109887
0.9722	High Similarity	NPC281563
0.9722	High Similarity	NPC477328
0.9722	High Similarity	NPC475425
0.9722	High Similarity	NPC477325
0.9722	High Similarity	NPC477326
0.9589	High Similarity	NPC477346
0.9589	High Similarity	NPC294748
0.9589	High Similarity	NPC22742
0.9589	High Similarity	NPC158302
0.9589	High Similarity	NPC477344
0.9589	High Similarity	NPC146992
0.9589	High Similarity	NPC85759
0.9571	High Similarity	NPC225748
0.9571	High Similarity	NPC169085
0.9571	High Similarity	NPC163812
0.9571	High Similarity	NPC39266
0.9571	High Similarity	NPC206823
0.9571	High Similarity	NPC9763
0.9459	High Similarity	NPC267592
0.9333	High Similarity	NPC475270
0.9333	High Similarity	NPC477347
0.9333	High Similarity	NPC475327
0.9333	High Similarity	NPC169345
0.9333	High Similarity	NPC269318
0.9333	High Similarity	NPC290012
0.9333	High Similarity	NPC224953
0.9333	High Similarity	NPC472204
0.9333	High Similarity	NPC477319
0.9333	High Similarity	NPC123204
0.9333	High Similarity	NPC173328
0.9333	High Similarity	NPC143421
0.9333	High Similarity	NPC477331
0.9333	High Similarity	NPC27289
0.9333	High Similarity	NPC475667
0.9333	High Similarity	NPC89843
0.9333	High Similarity	NPC476087
0.9333	High Similarity	NPC119583
0.9333	High Similarity	NPC472203
0.9333	High Similarity	NPC44782
0.9333	High Similarity	NPC126685
0.9333	High Similarity	NPC183888
0.9333	High Similarity	NPC186992
0.9333	High Similarity	NPC477318
0.9333	High Similarity	NPC115013
0.9333	High Similarity	NPC238056
0.9333	High Similarity	NPC307400
0.9333	High Similarity	NPC477317
0.9333	High Similarity	NPC259294
0.9333	High Similarity	NPC472201
0.9333	High Similarity	NPC472205
0.9333	High Similarity	NPC297768
0.9333	High Similarity	NPC184915
0.9333	High Similarity	NPC472202
0.9333	High Similarity	NPC472200
0.9286	High Similarity	NPC53760
0.9286	High Similarity	NPC52268
0.9143	High Similarity	NPC285003
0.9143	High Similarity	NPC241265
0.9143	High Similarity	NPC211428
0.9091	High Similarity	NPC472352
0.9091	High Similarity	NPC477332
0.9091	High Similarity	NPC60849
0.9	High Similarity	NPC67099
0.9	High Similarity	NPC97736
0.9	High Similarity	NPC250619
0.9	High Similarity	NPC50228
0.8857	High Similarity	NPC206601
0.8571	High Similarity	NPC471760
0.8571	High Similarity	NPC76881
0.8571	High Similarity	NPC12040
0.8571	High Similarity	NPC190418
0.8571	High Similarity	NPC471761
0.8514	High Similarity	NPC291228
0.8514	High Similarity	NPC308096
0.8378	Intermediate Similarity	NPC184550
0.8378	Intermediate Similarity	NPC185419
0.8286	Intermediate Similarity	NPC325773
0.8235	Intermediate Similarity	NPC477349
0.8046	Intermediate Similarity	NPC44682
0.8046	Intermediate Similarity	NPC238264
0.8046	Intermediate Similarity	NPC477345
0.8046	Intermediate Similarity	NPC163409
0.8046	Intermediate Similarity	NPC477348
0.8025	Intermediate Similarity	NPC248415
0.8	Intermediate Similarity	NPC477762
0.8	Intermediate Similarity	NPC477757
0.8	Intermediate Similarity	NPC477753
0.8	Intermediate Similarity	NPC477763
0.8	Intermediate Similarity	NPC477755
0.8	Intermediate Similarity	NPC477750
0.7927	Intermediate Similarity	NPC156089
0.7927	Intermediate Similarity	NPC470313
0.7927	Intermediate Similarity	NPC473500
0.7927	Intermediate Similarity	NPC38295
0.7917	Intermediate Similarity	NPC6848
0.7865	Intermediate Similarity	NPC476066
0.7865	Intermediate Similarity	NPC475525
0.7865	Intermediate Similarity	NPC475164
0.7865	Intermediate Similarity	NPC475540
0.7865	Intermediate Similarity	NPC473765
0.7865	Intermediate Similarity	NPC475375
0.7865	Intermediate Similarity	NPC473605
0.7865	Intermediate Similarity	NPC475593
0.7865	Intermediate Similarity	NPC475241
0.7714	Intermediate Similarity	NPC317023
0.7683	Intermediate Similarity	NPC21693
0.7683	Intermediate Similarity	NPC236649
0.7571	Intermediate Similarity	NPC472025
0.7558	Intermediate Similarity	NPC51662
0.7467	Intermediate Similarity	NPC477752
0.7467	Intermediate Similarity	NPC477756
0.7467	Intermediate Similarity	NPC477764
0.7467	Intermediate Similarity	NPC477751
0.7429	Intermediate Similarity	NPC148424
0.7368	Intermediate Similarity	NPC477754
0.7368	Intermediate Similarity	NPC477759
0.7368	Intermediate Similarity	NPC477761
0.7368	Intermediate Similarity	NPC477758
0.7368	Intermediate Similarity	NPC477760
0.7326	Intermediate Similarity	NPC83839
0.7241	Intermediate Similarity	NPC470657
0.7222	Intermediate Similarity	NPC320032
0.7222	Intermediate Similarity	NPC34877
0.7222	Intermediate Similarity	NPC290179
0.7222	Intermediate Similarity	NPC322855
0.7209	Intermediate Similarity	NPC288471
0.7195	Intermediate Similarity	NPC110813
0.7159	Intermediate Similarity	NPC31349
0.7159	Intermediate Similarity	NPC314364
0.7143	Intermediate Similarity	NPC32148
0.7143	Intermediate Similarity	NPC23155
0.7143	Intermediate Similarity	NPC303727
0.7143	Intermediate Similarity	NPC469937
0.7143	Intermediate Similarity	NPC53463
0.7143	Intermediate Similarity	NPC320588
0.7143	Intermediate Similarity	NPC126753
0.7113	Intermediate Similarity	NPC469827
0.7108	Intermediate Similarity	NPC133377
0.7071	Intermediate Similarity	NPC207693
0.7067	Intermediate Similarity	NPC268243
0.7011	Intermediate Similarity	NPC253975
0.7011	Intermediate Similarity	NPC192025
0.7011	Intermediate Similarity	NPC125253
0.7	Intermediate Similarity	NPC145112
0.7	Intermediate Similarity	NPC67660
0.7	Intermediate Similarity	NPC58629
0.7	Intermediate Similarity	NPC157514
0.7	Intermediate Similarity	NPC242073
0.7	Intermediate Similarity	NPC22709
0.7	Intermediate Similarity	NPC246558
0.7	Intermediate Similarity	NPC165198
0.7	Intermediate Similarity	NPC89145
0.7	Intermediate Similarity	NPC107914
0.7	Intermediate Similarity	NPC269166
0.6989	Remote Similarity	NPC215570
0.6988	Remote Similarity	NPC474003
0.6979	Remote Similarity	NPC188453
0.6979	Remote Similarity	NPC42320
0.697	Remote Similarity	NPC287269
0.6957	Remote Similarity	NPC320089
0.6939	Remote Similarity	NPC470519
0.6939	Remote Similarity	NPC231271
0.6931	Remote Similarity	NPC470622
0.6931	Remote Similarity	NPC471431
0.6915	Remote Similarity	NPC143446
0.6907	Remote Similarity	NPC310031
0.6907	Remote Similarity	NPC80191
0.69	Remote Similarity	NPC469826
0.6889	Remote Similarity	NPC470009
0.6875	Remote Similarity	NPC321873
0.6869	Remote Similarity	NPC184805
0.6869	Remote Similarity	NPC273189
0.6848	Remote Similarity	NPC110072
0.6842	Remote Similarity	NPC472273
0.6832	Remote Similarity	NPC236753
0.6832	Remote Similarity	NPC228190
0.6832	Remote Similarity	NPC469825
0.6804	Remote Similarity	NPC476611
0.68	Remote Similarity	NPC471430
0.68	Remote Similarity	NPC472026
0.68	Remote Similarity	NPC475234
0.68	Remote Similarity	NPC40716
0.68	Remote Similarity	NPC475630
0.68	Remote Similarity	NPC138219
0.6796	Remote Similarity	NPC157571
0.6771	Remote Similarity	NPC209798
0.6771	Remote Similarity	NPC471375
0.6771	Remote Similarity	NPC471374
0.6768	Remote Similarity	NPC267637

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 NPC477350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	834
0.1-0.2	4326
0.2-0.3	2737
0.3-0.4	777
0.4-0.5	272
0.5-0.6	154
0.6-0.7	47
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
0.8333	Intermediate Similarity	NPD7329	Approved
0.8	Intermediate Similarity	NPD6123	Approved
0.7342	Intermediate Similarity	NPD3181	Approved
0.7143	Intermediate Similarity	NPD3730	Approved
0.7143	Intermediate Similarity	NPD896	Approved
0.7143	Intermediate Similarity	NPD7346	Approved
0.7143	Intermediate Similarity	NPD897	Approved
0.7143	Intermediate Similarity	NPD898	Approved
0.7143	Intermediate Similarity	NPD3728	Approved
0.7	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD893	Approved
0.7	Intermediate Similarity	NPD891	Phase 3
0.7	Intermediate Similarity	NPD888	Phase 3
0.7	Intermediate Similarity	NPD892	Phase 3
0.6857	Remote Similarity	NPD2269	Approved
0.6714	Remote Similarity	NPD905	Approved
0.6714	Remote Similarity	NPD904	Phase 3
0.66	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8133	Approved
0.6566	Remote Similarity	NPD8086	Approved
0.6566	Remote Similarity	NPD7139	Approved
0.6566	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7140	Approved
0.6566	Remote Similarity	NPD8084	Approved
0.6566	Remote Similarity	NPD8082	Approved
0.6566	Remote Similarity	NPD8085	Approved
0.6566	Remote Similarity	NPD8139	Approved
0.6566	Remote Similarity	NPD8083	Approved
0.6566	Remote Similarity	NPD8138	Approved
0.6535	Remote Similarity	NPD8393	Approved
0.6528	Remote Similarity	NPD887	Approved
0.6528	Remote Similarity	NPD895	Approved
0.6528	Remote Similarity	NPD889	Approved
0.6528	Remote Similarity	NPD894	Approved
0.65	Remote Similarity	NPD8275	Approved
0.65	Remote Similarity	NPD8276	Approved
0.6486	Remote Similarity	NPD2267	Suspended
0.6436	Remote Similarity	NPD8081	Approved
0.641	Remote Similarity	NPD8961	Approved
0.6381	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3669	Approved
0.6333	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7909	Approved
0.6311	Remote Similarity	NPD8140	Approved
0.6311	Remote Similarity	NPD8307	Discontinued
0.6286	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8305	Approved
0.619	Remote Similarity	NPD6941	Approved
0.619	Remote Similarity	NPD8306	Approved
0.6184	Remote Similarity	NPD369	Approved
0.6161	Remote Similarity	NPD8517	Approved
0.6161	Remote Similarity	NPD8516	Approved
0.6161	Remote Similarity	NPD8515	Approved
0.6132	Remote Similarity	NPD8087	Discontinued
0.6111	Remote Similarity	NPD1779	Approved
0.6111	Remote Similarity	NPD1780	Approved
0.6095	Remote Similarity	NPD6686	Approved
0.6091	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD8171	Discontinued
0.6018	Remote Similarity	NPD8513	Phase 3
0.6	Remote Similarity	NPD8997	Approved
0.6	Remote Similarity	NPD8999	Phase 3
0.6	Remote Similarity	NPD8998	Phase 2
0.6	Remote Similarity	NPD8993	Phase 1
0.6	Remote Similarity	NPD9000	Phase 3
0.5974	Remote Similarity	NPD8959	Approved
0.5929	Remote Similarity	NPD8346	Approved
0.5929	Remote Similarity	NPD8347	Approved
0.5929	Remote Similarity	NPD8345	Approved
0.5918	Remote Similarity	NPD1446	Phase 3
0.5918	Remote Similarity	NPD1447	Phase 3
0.5913	Remote Similarity	NPD8328	Phase 3
0.59	Remote Similarity	NPD6428	Approved
0.5876	Remote Similarity	NPD6698	Approved
0.5876	Remote Similarity	NPD46	Approved
0.5857	Remote Similarity	NPD2699	Approved
0.5849	Remote Similarity	NPD6412	Phase 2
0.5844	Remote Similarity	NPD73	Approved
0.5833	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8966	Approved
0.5833	Remote Similarity	NPD8965	Approved
0.5804	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD847	Phase 1
0.5789	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD2255	Approved
0.5769	Remote Similarity	NPD8301	Approved
0.5769	Remote Similarity	NPD8300	Approved
0.5714	Remote Similarity	NPD6940	Discontinued
0.5686	Remote Similarity	NPD881	Approved
0.5682	Remote Similarity	NPD1811	Approved
0.5682	Remote Similarity	NPD1810	Approved
0.5658	Remote Similarity	NPD9036	Phase 3
0.5658	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7983	Approved
0.5631	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD3716	Discontinued
0.5604	Remote Similarity	NPD4238	Approved
0.5604	Remote Similarity	NPD4802	Phase 2
0.5603	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.56	Remote Similarity	NPD1399	Approved
0.56	Remote Similarity	NPD1400	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