NPASS Compound

Structure

NPC271207 OpenBabel07101718292D 32 34 0 0 1 0 0 0 0 0999 V2000 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7321 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4641 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -3.0000 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 11 2 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 11 1 0 0 0 0 8 22 1 0 0 0 0 9 24 1 0 0 0 0 10 29 1 0 0 0 0 10 30 1 0 0 0 0 11 12 1 0 0 0 0 12 2 1 1 0 0 0 12 13 1 0 0 0 0 13 3 1 1 0 0 0 13 32 1 0 0 0 0 14 9 1 1 0 0 0 14 21 1 0 0 0 0 14 31 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 6 0 0 0 16 20 1 0 0 0 0 16 31 1 6 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 17 25 1 6 0 0 0 18 21 1 0 0 0 0 18 27 1 1 0 0 0 19 23 2 3 0 0 0 19 26 1 0 0 0 0 20 23 1 6 0 0 0 20 30 1 0 0 0 0 22 28 1 6 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	459.25
Volume:	448.235
LogP:	2.023
LogD:	2.386
LogS:	-2.123
# Rotatable Bonds:	7
TPSA:	124.94
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	5.577
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.001
MDCK Permeability:	3.36812408932019e-05
Pgp-inhibitor:	0.081
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.333

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	42.729087829589844%
Volume Distribution (VD):	0.767
Pgp-substrate:	62.431396484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.144
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.614
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.578

ADMET: Excretion

Clearance (CL):	4.547
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.502
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.219
Carcinogencity:	0.116
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.127

Download Data

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

Natural Product: NPC271207

Natural Product ID:	NPC271207
*Common Name:**	Theopederin E
IUPAC Name:	(2S)-N-[(4R,4aS,6S,8S,8aR)-6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide
Synonyms:	Theopederin E
Standard InCHIKey:	OBDAALQFQJRDKI-SBZOUALISA-N
Standard InCHI:	InChI=1S/C22H37NO9/c1-11-8-22(28-7,32-13(3)12(11)2)17(25)19(26)23-20-16-15(29-10-30-20)18(27-6)21(4,5)14(9-24)31-16/h12-18,20,24-25H,1,8-10H2,2-7H3,(H,23,26)/t12-,13-,14-,15+,16+,17-,18-,20-,22-/m1/s1
SMILES:	CO[C@@H]1[C@H]2OCO[C@H]([C@H]2O[C@@H](C1(C)C)CO)N=C([C@H]([C@@]1(OC)CC(=C)[C@H]([C@H](O1)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497718
PubChem CID:	44583759
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002011] Pyranodioxins

*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
NPO33503	stylinos n. species	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10843596]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.0009	ug.mL-1	PMID[485006]

☑ 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 NPC271207 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	96
0.1-0.2	1032
0.2-0.3	9069
0.3-0.4	17072
0.4-0.5	9457
0.5-0.6	5317
0.6-0.7	614
0.7-0.8	31
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC255175
1.0	High Similarity	NPC225978
1.0	High Similarity	NPC206711
0.9674	High Similarity	NPC189629
0.8058	Intermediate Similarity	NPC477198
0.7843	Intermediate Similarity	NPC475646
0.7755	Intermediate Similarity	NPC470284
0.7745	Intermediate Similarity	NPC475503
0.7708	Intermediate Similarity	NPC476523
0.7525	Intermediate Similarity	NPC475603
0.7525	Intermediate Similarity	NPC61894
0.7436	Intermediate Similarity	NPC469943
0.7379	Intermediate Similarity	NPC470283
0.7212	Intermediate Similarity	NPC70323
0.7212	Intermediate Similarity	NPC256570
0.7212	Intermediate Similarity	NPC17290
0.7212	Intermediate Similarity	NPC192066
0.7212	Intermediate Similarity	NPC262312
0.7212	Intermediate Similarity	NPC35269
0.7212	Intermediate Similarity	NPC3568
0.7212	Intermediate Similarity	NPC23454
0.7207	Intermediate Similarity	NPC475150
0.7182	Intermediate Similarity	NPC475918
0.7143	Intermediate Similarity	NPC473578
0.7075	Intermediate Similarity	NPC197294
0.7075	Intermediate Similarity	NPC183449
0.7075	Intermediate Similarity	NPC8098
0.7075	Intermediate Similarity	NPC45313
0.7063	Intermediate Similarity	NPC280941
0.7063	Intermediate Similarity	NPC235772
0.704	Intermediate Similarity	NPC119794
0.704	Intermediate Similarity	NPC73829
0.7019	Intermediate Similarity	NPC473581
0.7019	Intermediate Similarity	NPC15851
0.7019	Intermediate Similarity	NPC111567
0.7019	Intermediate Similarity	NPC473950
0.7019	Intermediate Similarity	NPC475125
0.7019	Intermediate Similarity	NPC282705
0.7019	Intermediate Similarity	NPC186840
0.7019	Intermediate Similarity	NPC309898
0.7019	Intermediate Similarity	NPC263545
0.7019	Intermediate Similarity	NPC473604
0.7019	Intermediate Similarity	NPC182632
0.7018	Intermediate Similarity	NPC29501
0.6961	Remote Similarity	NPC470282
0.696	Remote Similarity	NPC475472
0.696	Remote Similarity	NPC139585
0.6957	Remote Similarity	NPC469865
0.6929	Remote Similarity	NPC75318
0.6923	Remote Similarity	NPC209047
0.6923	Remote Similarity	NPC43074
0.6923	Remote Similarity	NPC74672
0.6923	Remote Similarity	NPC242503
0.6923	Remote Similarity	NPC139782
0.6899	Remote Similarity	NPC243680
0.6899	Remote Similarity	NPC200788
0.6887	Remote Similarity	NPC54961
0.6887	Remote Similarity	NPC158445
0.6887	Remote Similarity	NPC156782
0.6887	Remote Similarity	NPC157353
0.6887	Remote Similarity	NPC282088
0.6875	Remote Similarity	NPC145899
0.6857	Remote Similarity	NPC270005
0.6857	Remote Similarity	NPC208537
0.685	Remote Similarity	NPC76999
0.685	Remote Similarity	NPC477072
0.6846	Remote Similarity	NPC180770
0.6846	Remote Similarity	NPC302276
0.6794	Remote Similarity	NPC210729
0.6794	Remote Similarity	NPC172365
0.6794	Remote Similarity	NPC82931
0.6767	Remote Similarity	NPC141669
0.6742	Remote Similarity	NPC162910
0.6735	Remote Similarity	NPC316807
0.6729	Remote Similarity	NPC72817
0.6729	Remote Similarity	NPC477927
0.67	Remote Similarity	NPC16090
0.6697	Remote Similarity	NPC76486
0.6692	Remote Similarity	NPC475394
0.6692	Remote Similarity	NPC475152
0.6692	Remote Similarity	NPC475584
0.6667	Remote Similarity	NPC166279
0.6667	Remote Similarity	NPC477199
0.6642	Remote Similarity	NPC284625
0.6642	Remote Similarity	NPC193579
0.6642	Remote Similarity	NPC298469
0.6642	Remote Similarity	NPC475892
0.6642	Remote Similarity	NPC69176
0.6634	Remote Similarity	NPC20072
0.6593	Remote Similarity	NPC298067
0.6593	Remote Similarity	NPC214821
0.6591	Remote Similarity	NPC265908
0.6587	Remote Similarity	NPC329919
0.6587	Remote Similarity	NPC477793
0.6579	Remote Similarity	NPC201128
0.6577	Remote Similarity	NPC64348
0.6577	Remote Similarity	NPC91497
0.6571	Remote Similarity	NPC248312
0.656	Remote Similarity	NPC94881
0.656	Remote Similarity	NPC48886
0.656	Remote Similarity	NPC265275
0.6542	Remote Similarity	NPC302584
0.6525	Remote Similarity	NPC314306
0.6522	Remote Similarity	NPC36463
0.6522	Remote Similarity	NPC298005
0.6518	Remote Similarity	NPC263756
0.6518	Remote Similarity	NPC117714
0.6496	Remote Similarity	NPC61717
0.6496	Remote Similarity	NPC244380
0.6486	Remote Similarity	NPC56071
0.6486	Remote Similarity	NPC477928
0.6486	Remote Similarity	NPC70733
0.6481	Remote Similarity	NPC67398
0.6481	Remote Similarity	NPC91654
0.6481	Remote Similarity	NPC474835
0.6481	Remote Similarity	NPC474792
0.648	Remote Similarity	NPC296686
0.646	Remote Similarity	NPC76497
0.646	Remote Similarity	NPC272015
0.646	Remote Similarity	NPC30289
0.646	Remote Similarity	NPC213674
0.646	Remote Similarity	NPC256133
0.6455	Remote Similarity	NPC90583
0.6455	Remote Similarity	NPC472989
0.6449	Remote Similarity	NPC477865
0.6449	Remote Similarity	NPC477866
0.6449	Remote Similarity	NPC159876
0.6436	Remote Similarity	NPC471420
0.6436	Remote Similarity	NPC100697
0.6435	Remote Similarity	NPC309448
0.6434	Remote Similarity	NPC15249
0.6434	Remote Similarity	NPC25455
0.6422	Remote Similarity	NPC305160
0.6404	Remote Similarity	NPC123796
0.6396	Remote Similarity	NPC278506
0.6396	Remote Similarity	NPC473890
0.6396	Remote Similarity	NPC240372
0.6396	Remote Similarity	NPC243728
0.6396	Remote Similarity	NPC470684
0.6396	Remote Similarity	NPC470683
0.6385	Remote Similarity	NPC122819
0.6383	Remote Similarity	NPC477760
0.6383	Remote Similarity	NPC477758
0.6383	Remote Similarity	NPC477754
0.6383	Remote Similarity	NPC477761
0.6383	Remote Similarity	NPC477759
0.6381	Remote Similarity	NPC470836
0.6379	Remote Similarity	NPC317534
0.6379	Remote Similarity	NPC230507
0.6379	Remote Similarity	NPC78034
0.6379	Remote Similarity	NPC190395
0.6379	Remote Similarity	NPC283829
0.6379	Remote Similarity	NPC94272
0.6379	Remote Similarity	NPC257964
0.6379	Remote Similarity	NPC113044
0.6379	Remote Similarity	NPC470432
0.6379	Remote Similarity	NPC14704
0.6379	Remote Similarity	NPC305423
0.6379	Remote Similarity	NPC161676
0.6372	Remote Similarity	NPC188453
0.6372	Remote Similarity	NPC470168
0.6372	Remote Similarity	NPC42320
0.6364	Remote Similarity	NPC297058
0.6364	Remote Similarity	NPC172197
0.6364	Remote Similarity	NPC274293
0.6355	Remote Similarity	NPC473058
0.6349	Remote Similarity	NPC469494
0.6348	Remote Similarity	NPC470768
0.6348	Remote Similarity	NPC471435
0.6348	Remote Similarity	NPC230948
0.6348	Remote Similarity	NPC74035
0.6348	Remote Similarity	NPC109792
0.6348	Remote Similarity	NPC57065
0.6348	Remote Similarity	NPC475521
0.6348	Remote Similarity	NPC476361
0.6348	Remote Similarity	NPC148603
0.6348	Remote Similarity	NPC221562
0.6348	Remote Similarity	NPC54521
0.6348	Remote Similarity	NPC473734
0.6348	Remote Similarity	NPC470885
0.6348	Remote Similarity	NPC476360
0.6348	Remote Similarity	NPC187400
0.6348	Remote Similarity	NPC471434
0.6344	Remote Similarity	NPC147292
0.6339	Remote Similarity	NPC158088
0.6336	Remote Similarity	NPC150057
0.6336	Remote Similarity	NPC147753
0.6325	Remote Similarity	NPC98696
0.6325	Remote Similarity	NPC126147
0.6316	Remote Similarity	NPC312553
0.6316	Remote Similarity	NPC288694
0.6316	Remote Similarity	NPC136816
0.6316	Remote Similarity	NPC159036
0.6306	Remote Similarity	NPC207617
0.6296	Remote Similarity	NPC261990
0.6296	Remote Similarity	NPC474249
0.6293	Remote Similarity	NPC470763
0.6293	Remote Similarity	NPC474569
0.6293	Remote Similarity	NPC269627
0.6293	Remote Similarity	NPC173859

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 NPC271207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	84
0.1-0.2	764
0.2-0.3	4229
0.3-0.4	3082
0.4-0.5	747
0.5-0.6	205
0.6-0.7	38
0.7-0.8	1
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
0.7054	Intermediate Similarity	NPD8174	Phase 2
0.6923	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6421	Discontinued
0.6525	Remote Similarity	NPD6430	Approved
0.6525	Remote Similarity	NPD6429	Approved
0.6435	Remote Similarity	NPD5357	Phase 1
0.6385	Remote Similarity	NPD8449	Approved
0.6371	Remote Similarity	NPD8267	Approved
0.6371	Remote Similarity	NPD8266	Approved
0.6371	Remote Similarity	NPD8269	Approved
0.6371	Remote Similarity	NPD8268	Approved
0.6357	Remote Similarity	NPD8390	Approved
0.6357	Remote Similarity	NPD8391	Approved
0.6357	Remote Similarity	NPD8392	Approved
0.6336	Remote Similarity	NPD8450	Suspended
0.632	Remote Similarity	NPD6436	Phase 3
0.6311	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5376	Approved
0.6271	Remote Similarity	NPD8305	Approved
0.6271	Remote Similarity	NPD8306	Approved
0.622	Remote Similarity	NPD8299	Approved
0.622	Remote Similarity	NPD8342	Approved
0.622	Remote Similarity	NPD8341	Approved
0.622	Remote Similarity	NPD8340	Approved
0.6216	Remote Similarity	NPD5378	Approved
0.6216	Remote Similarity	NPD5377	Approved
0.6216	Remote Similarity	NPD5381	Approved
0.6172	Remote Similarity	NPD8451	Approved
0.6161	Remote Similarity	NPD6428	Approved
0.6154	Remote Similarity	NPD6640	Phase 3
0.6129	Remote Similarity	NPD7641	Discontinued
0.6124	Remote Similarity	NPD8448	Approved
0.6122	Remote Similarity	NPD3187	Discontinued
0.6121	Remote Similarity	NPD8276	Approved
0.6121	Remote Similarity	NPD8275	Approved
0.6111	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD8307	Discontinued
0.6102	Remote Similarity	NPD8140	Approved
0.6082	Remote Similarity	NPD9445	Approved
0.6063	Remote Similarity	NPD8080	Discontinued
0.6034	Remote Similarity	NPD8083	Approved
0.6034	Remote Similarity	NPD8138	Approved
0.6034	Remote Similarity	NPD8139	Approved
0.6034	Remote Similarity	NPD8085	Approved
0.6034	Remote Similarity	NPD8084	Approved
0.6034	Remote Similarity	NPD8086	Approved
0.6034	Remote Similarity	NPD8082	Approved
0.6019	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD8393	Approved
0.6	Remote Similarity	NPD3168	Discontinued
0.5983	Remote Similarity	NPD1407	Approved
0.595	Remote Similarity	NPD8087	Discontinued
0.5935	Remote Similarity	NPD8133	Approved
0.5932	Remote Similarity	NPD8081	Approved
0.5929	Remote Similarity	NPD7844	Discontinued
0.5917	Remote Similarity	NPD6686	Approved
0.5909	Remote Similarity	NPD3716	Discontinued
0.5906	Remote Similarity	NPD8345	Approved
0.5906	Remote Similarity	NPD8346	Approved
0.5906	Remote Similarity	NPD8347	Approved
0.5897	Remote Similarity	NPD7140	Approved
0.5897	Remote Similarity	NPD7139	Approved
0.5897	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD7829	Approved
0.5891	Remote Similarity	NPD7830	Approved
0.5877	Remote Similarity	NPD3189	Approved
0.5877	Remote Similarity	NPD3190	Approved
0.5877	Remote Similarity	NPD3191	Approved
0.5865	Remote Similarity	NPD6914	Discontinued
0.5862	Remote Similarity	NPD4836	Approved
0.5862	Remote Similarity	NPD4835	Approved
0.5862	Remote Similarity	NPD4838	Approved
0.5862	Remote Similarity	NPD4837	Approved
0.5847	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6412	Phase 2
0.5806	Remote Similarity	NPD3731	Phase 3
0.5804	Remote Similarity	NPD7625	Phase 1
0.5772	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8074	Phase 3
0.5752	Remote Similarity	NPD8171	Discontinued
0.5752	Remote Similarity	NPD1447	Phase 3
0.5752	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD1446	Phase 3
0.5738	Remote Similarity	NPD6941	Approved
0.5736	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD4832	Approved
0.5714	Remote Similarity	NPD4831	Approved
0.5714	Remote Similarity	NPD4830	Approved
0.5693	Remote Similarity	NPD8415	Approved
0.569	Remote Similarity	NPD4282	Approved
0.5676	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD8377	Approved
0.5659	Remote Similarity	NPD8294	Approved
0.5649	Remote Similarity	NPD7642	Approved
0.5641	Remote Similarity	NPD2255	Approved
0.5641	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.562	Remote Similarity	NPD4211	Phase 1
0.5615	Remote Similarity	NPD8378	Approved
0.5615	Remote Similarity	NPD8380	Approved
0.5615	Remote Similarity	NPD8296	Approved
0.5615	Remote Similarity	NPD8379	Approved
0.5615	Remote Similarity	NPD8033	Approved
0.5615	Remote Similarity	NPD8335	Approved
0.561	Remote Similarity	NPD8132	Clinical (unspecified phase)

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