NPASS Compound

Structure

NPC239127 OpenBabel07101718272D 24 24 0 0 1 0 0 0 0 0999 V2000 6.4721 -3.6919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2474 -2.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5289 2.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7650 -4.3990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3496 -1.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3155 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0908 -0.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7991 -4.1402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5743 -2.9154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1248 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5403 -3.1742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6594 1.1088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 6 1 0 0 0 0 2 15 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 16 3 1 1 0 0 0 16 17 1 0 0 0 0 17 13 1 1 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 12 1 1 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 23 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.22
Volume:	364.665
LogP:	3.202
LogD:	3.376
LogS:	-3.402
# Rotatable Bonds:	10
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	4.512
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.452
MDCK Permeability:	3.8423728256020695e-05
Pgp-inhibitor:	0.942
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.45
Plasma Protein Binding (PPB):	86.99878692626953%
Volume Distribution (VD):	1.861
Pgp-substrate:	5.8948211669921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.665
CYP2C19-inhibitor:	0.378
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.393
CYP2D6-inhibitor:	0.067
CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.829
CYP3A4-substrate:	0.501

ADMET: Excretion

Clearance (CL):	12.83
Half-life (T1/2):	0.732

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.445
Drug-inuced Liver Injury (DILI):	0.514
AMES Toxicity:	0.636
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.327
Skin Sensitization:	0.952
Carcinogencity:	0.876
Eye Corrosion:	0.626
Eye Irritation:	0.545
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC239127

Natural Product ID:	NPC239127
*Common Name:**	Manadoperoxide B
IUPAC Name:	methyl 2-[(3S,4S,6R)-6-methoxy-4-methyl-6-[(4E,6E)-6-methylnona-4,6-dienyl]dioxan-3-yl]acetate
Synonyms:
Standard InCHIKey:	MMZGNYMATSQASW-YRWIGPPUSA-N
Standard InCHI:	InChI=1S/C19H32O5/c1-6-10-15(2)11-8-7-9-12-19(22-5)14-16(3)17(23-24-19)13-18(20)21-4/h8,10-11,16-17H,6-7,9,12-14H2,1-5H3/b11-8+,15-10+/t16-,17-,19+/m0/s1
SMILES:	CC/C=C(C)/C=C/CCC[C@@]1(C[C@H](C)[C@H](CC(=O)OC)OO1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1164344
PubChem CID:	46850010
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO33403	plakortis cfr. simplex	Species	Plakinidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[20521782]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6760.0	nM	PMID[555590]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3690.0	nM	PMID[555590]

☑ 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 NPC239127 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	182
0.1-0.2	993
0.2-0.3	5244
0.3-0.4	14633
0.4-0.5	11143
0.5-0.6	8059
0.6-0.7	2266
0.7-0.8	142
0.8-0.85	19
0.85-0.9	8
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC255060
0.9296	High Similarity	NPC167145
0.9178	High Similarity	NPC474447
0.9167	High Similarity	NPC330016
0.8919	High Similarity	NPC266119
0.88	High Similarity	NPC476325
0.88	High Similarity	NPC476264
0.8701	High Similarity	NPC469920
0.8684	High Similarity	NPC121200
0.8667	High Similarity	NPC469514
0.8553	High Similarity	NPC281296
0.8514	High Similarity	NPC472018
0.8514	High Similarity	NPC238425
0.8514	High Similarity	NPC474543
0.84	Intermediate Similarity	NPC474551
0.8375	Intermediate Similarity	NPC69469
0.8354	Intermediate Similarity	NPC475481
0.8354	Intermediate Similarity	NPC79277
0.8354	Intermediate Similarity	NPC476988
0.8333	Intermediate Similarity	NPC82488
0.8333	Intermediate Similarity	NPC308545
0.8243	Intermediate Similarity	NPC69462
0.8243	Intermediate Similarity	NPC472017
0.8182	Intermediate Similarity	NPC59602
0.8182	Intermediate Similarity	NPC476987
0.8182	Intermediate Similarity	NPC152754
0.8125	Intermediate Similarity	NPC14044
0.8125	Intermediate Similarity	NPC117960
0.8125	Intermediate Similarity	NPC172309
0.8108	Intermediate Similarity	NPC107130
0.8072	Intermediate Similarity	NPC477994
0.8072	Intermediate Similarity	NPC477993
0.8052	Intermediate Similarity	NPC60718
0.8052	Intermediate Similarity	NPC199445
0.8	Intermediate Similarity	NPC475310
0.7976	Intermediate Similarity	NPC86005
0.7949	Intermediate Similarity	NPC474316
0.7949	Intermediate Similarity	NPC476985
0.7949	Intermediate Similarity	NPC475744
0.7927	Intermediate Similarity	NPC475989
0.7875	Intermediate Similarity	NPC113363
0.7875	Intermediate Similarity	NPC268502
0.7875	Intermediate Similarity	NPC254996
0.7857	Intermediate Similarity	NPC476104
0.7857	Intermediate Similarity	NPC476982
0.7848	Intermediate Similarity	NPC122847
0.7848	Intermediate Similarity	NPC145898
0.7791	Intermediate Similarity	NPC97577
0.7738	Intermediate Similarity	NPC471344
0.7711	Intermediate Similarity	NPC476983
0.7662	Intermediate Similarity	NPC126061
0.7662	Intermediate Similarity	NPC320119
0.7654	Intermediate Similarity	NPC263574
0.7654	Intermediate Similarity	NPC158565
0.7654	Intermediate Similarity	NPC469747
0.7647	Intermediate Similarity	NPC262085
0.7614	Intermediate Similarity	NPC36491
0.7606	Intermediate Similarity	NPC226602
0.7606	Intermediate Similarity	NPC472020
0.7606	Intermediate Similarity	NPC472019
0.7586	Intermediate Similarity	NPC256902
0.7586	Intermediate Similarity	NPC118193
0.7586	Intermediate Similarity	NPC469866
0.7586	Intermediate Similarity	NPC471342
0.7561	Intermediate Similarity	NPC476265
0.7561	Intermediate Similarity	NPC274522
0.7558	Intermediate Similarity	NPC477959
0.7531	Intermediate Similarity	NPC476986
0.7531	Intermediate Similarity	NPC218817
0.7531	Intermediate Similarity	NPC470905
0.7531	Intermediate Similarity	NPC11796
0.7529	Intermediate Similarity	NPC474369
0.7528	Intermediate Similarity	NPC478037
0.7528	Intermediate Similarity	NPC478036
0.75	Intermediate Similarity	NPC472021
0.7473	Intermediate Similarity	NPC180722
0.7473	Intermediate Similarity	NPC165332
0.7473	Intermediate Similarity	NPC195645
0.7471	Intermediate Similarity	NPC201046
0.7467	Intermediate Similarity	NPC284447
0.7412	Intermediate Similarity	NPC475193
0.7412	Intermediate Similarity	NPC471343
0.7412	Intermediate Similarity	NPC120158
0.7407	Intermediate Similarity	NPC240170
0.7407	Intermediate Similarity	NPC120776
0.7407	Intermediate Similarity	NPC474760
0.7407	Intermediate Similarity	NPC469867
0.7403	Intermediate Similarity	NPC199557
0.7391	Intermediate Similarity	NPC475438
0.7381	Intermediate Similarity	NPC475395
0.7381	Intermediate Similarity	NPC476984
0.7375	Intermediate Similarity	NPC228978
0.7375	Intermediate Similarity	NPC324762
0.7375	Intermediate Similarity	NPC475861
0.7349	Intermediate Similarity	NPC103634
0.7342	Intermediate Similarity	NPC470237
0.7342	Intermediate Similarity	NPC326024
0.7333	Intermediate Similarity	NPC326268
0.7333	Intermediate Similarity	NPC318420
0.7326	Intermediate Similarity	NPC76333
0.7317	Intermediate Similarity	NPC127526
0.7308	Intermediate Similarity	NPC472955
0.7303	Intermediate Similarity	NPC51653
0.7303	Intermediate Similarity	NPC313670
0.7297	Intermediate Similarity	NPC54925
0.7294	Intermediate Similarity	NPC16488
0.7294	Intermediate Similarity	NPC475947
0.7294	Intermediate Similarity	NPC476100
0.7286	Intermediate Similarity	NPC228473
0.7284	Intermediate Similarity	NPC266159
0.7284	Intermediate Similarity	NPC472967
0.7253	Intermediate Similarity	NPC5418
0.7253	Intermediate Similarity	NPC471078
0.7253	Intermediate Similarity	NPC473431
0.7253	Intermediate Similarity	NPC473280
0.7253	Intermediate Similarity	NPC473435
0.725	Intermediate Similarity	NPC306928
0.7241	Intermediate Similarity	NPC469483
0.7241	Intermediate Similarity	NPC315395
0.7241	Intermediate Similarity	NPC316426
0.7241	Intermediate Similarity	NPC475753
0.7241	Intermediate Similarity	NPC116575
0.7234	Intermediate Similarity	NPC469871
0.7234	Intermediate Similarity	NPC469870
0.7229	Intermediate Similarity	NPC28319
0.7229	Intermediate Similarity	NPC471740
0.7195	Intermediate Similarity	NPC107668
0.7195	Intermediate Similarity	NPC97516
0.7179	Intermediate Similarity	NPC329656
0.7179	Intermediate Similarity	NPC477448
0.7179	Intermediate Similarity	NPC473772
0.7179	Intermediate Similarity	NPC296522
0.7179	Intermediate Similarity	NPC144511
0.7179	Intermediate Similarity	NPC477449
0.7176	Intermediate Similarity	NPC474605
0.7176	Intermediate Similarity	NPC476292
0.7176	Intermediate Similarity	NPC85772
0.7174	Intermediate Similarity	NPC54905
0.7174	Intermediate Similarity	NPC314009
0.716	Intermediate Similarity	NPC469414
0.716	Intermediate Similarity	NPC329826
0.7159	Intermediate Similarity	NPC471739
0.7125	Intermediate Similarity	NPC135703
0.7108	Intermediate Similarity	NPC474341
0.7108	Intermediate Similarity	NPC4827
0.7105	Intermediate Similarity	NPC306805
0.7105	Intermediate Similarity	NPC215987
0.7097	Intermediate Similarity	NPC106425
0.7097	Intermediate Similarity	NPC471153
0.7097	Intermediate Similarity	NPC122324
0.7097	Intermediate Similarity	NPC151725
0.7093	Intermediate Similarity	NPC312480
0.7093	Intermediate Similarity	NPC170377
0.7089	Intermediate Similarity	NPC476660
0.7083	Intermediate Similarity	NPC475091
0.7079	Intermediate Similarity	NPC473151
0.7073	Intermediate Similarity	NPC471726
0.7073	Intermediate Similarity	NPC12740
0.7073	Intermediate Similarity	NPC110461
0.7073	Intermediate Similarity	NPC301525
0.7073	Intermediate Similarity	NPC279537
0.7073	Intermediate Similarity	NPC899
0.7073	Intermediate Similarity	NPC474527
0.7067	Intermediate Similarity	NPC474552
0.7059	Intermediate Similarity	NPC47031
0.7059	Intermediate Similarity	NPC255580
0.7059	Intermediate Similarity	NPC42470
0.7059	Intermediate Similarity	NPC141810
0.7059	Intermediate Similarity	NPC25684
0.7059	Intermediate Similarity	NPC474955
0.7059	Intermediate Similarity	NPC39411
0.7059	Intermediate Similarity	NPC88735
0.7059	Intermediate Similarity	NPC471325
0.7059	Intermediate Similarity	NPC286229
0.7059	Intermediate Similarity	NPC281949
0.7059	Intermediate Similarity	NPC301477
0.7051	Intermediate Similarity	NPC273508
0.7051	Intermediate Similarity	NPC209327
0.7045	Intermediate Similarity	NPC234038
0.7045	Intermediate Similarity	NPC475181
0.7045	Intermediate Similarity	NPC104961
0.7045	Intermediate Similarity	NPC70555
0.7045	Intermediate Similarity	NPC70422
0.7045	Intermediate Similarity	NPC198314
0.7042	Intermediate Similarity	NPC28779
0.7042	Intermediate Similarity	NPC223677
0.7042	Intermediate Similarity	NPC128061
0.7042	Intermediate Similarity	NPC10316
0.7042	Intermediate Similarity	NPC200845
0.7037	Intermediate Similarity	NPC140287
0.7037	Intermediate Similarity	NPC166797
0.7033	Intermediate Similarity	NPC472199
0.7024	Intermediate Similarity	NPC617
0.7024	Intermediate Similarity	NPC264227
0.7024	Intermediate Similarity	NPC472965
0.7024	Intermediate Similarity	NPC63649
0.7024	Intermediate Similarity	NPC19841
0.7011	Intermediate Similarity	NPC139566
0.7011	Intermediate Similarity	NPC196487
0.7011	Intermediate Similarity	NPC9868

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 NPC239127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1350
0.2-0.3	3893
0.3-0.4	2531
0.4-0.5	739
0.5-0.6	405
0.6-0.7	58
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
0.7791	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6101	Approved
0.7614	Intermediate Similarity	NPD6411	Approved
0.7473	Intermediate Similarity	NPD7839	Suspended
0.7416	Intermediate Similarity	NPD7983	Approved
0.7375	Intermediate Similarity	NPD8039	Approved
0.7333	Intermediate Similarity	NPD5778	Approved
0.7333	Intermediate Similarity	NPD5779	Approved
0.7262	Intermediate Similarity	NPD5369	Approved
0.7176	Intermediate Similarity	NPD6435	Approved
0.7143	Intermediate Similarity	NPD5368	Approved
0.7093	Intermediate Similarity	NPD7154	Phase 3
0.6977	Remote Similarity	NPD4270	Approved
0.6977	Remote Similarity	NPD4269	Approved
0.6923	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD46	Approved
0.6897	Remote Similarity	NPD5362	Discontinued
0.6854	Remote Similarity	NPD5786	Approved
0.6782	Remote Similarity	NPD5209	Approved
0.6744	Remote Similarity	NPD4819	Approved
0.6744	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4822	Approved
0.6744	Remote Similarity	NPD4820	Approved
0.6744	Remote Similarity	NPD4252	Approved
0.6744	Remote Similarity	NPD4821	Approved
0.6742	Remote Similarity	NPD5363	Approved
0.6714	Remote Similarity	NPD28	Approved
0.6714	Remote Similarity	NPD29	Approved
0.6706	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4268	Approved
0.6706	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD6422	Discontinued
0.6667	Remote Similarity	NPD7637	Suspended
0.6559	Remote Similarity	NPD5785	Approved
0.6538	Remote Similarity	NPD3197	Phase 1
0.6526	Remote Similarity	NPD5282	Discontinued
0.6512	Remote Similarity	NPD3732	Approved
0.6484	Remote Similarity	NPD7521	Approved
0.6484	Remote Similarity	NPD7334	Approved
0.6484	Remote Similarity	NPD5330	Approved
0.6484	Remote Similarity	NPD6409	Approved
0.6484	Remote Similarity	NPD6684	Approved
0.6484	Remote Similarity	NPD7146	Approved
0.6458	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4266	Approved
0.6438	Remote Similarity	NPD3195	Phase 2
0.6438	Remote Similarity	NPD3194	Approved
0.6438	Remote Similarity	NPD3196	Approved
0.6429	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6399	Phase 3
0.6404	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7838	Discovery
0.6375	Remote Similarity	NPD7331	Phase 2
0.6364	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7900	Approved
0.6354	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6672	Approved
0.6344	Remote Similarity	NPD5737	Approved
0.6344	Remote Similarity	NPD6903	Approved
0.6344	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5331	Approved
0.6333	Remote Similarity	NPD5332	Approved
0.6329	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD3172	Approved
0.6292	Remote Similarity	NPD4790	Discontinued
0.6277	Remote Similarity	NPD5370	Suspended
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4250	Approved
0.6237	Remote Similarity	NPD4251	Approved
0.6211	Remote Similarity	NPD3672	Approved
0.6211	Remote Similarity	NPD3673	Approved
0.6207	Remote Similarity	NPD4756	Discovery
0.6196	Remote Similarity	NPD1694	Approved
0.6196	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7748	Approved
0.618	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7902	Approved
0.6161	Remote Similarity	NPD8513	Phase 3
0.6161	Remote Similarity	NPD8516	Approved
0.6161	Remote Similarity	NPD8517	Approved
0.6161	Remote Similarity	NPD8515	Approved
0.6146	Remote Similarity	NPD6050	Approved
0.6146	Remote Similarity	NPD5284	Approved
0.6146	Remote Similarity	NPD5281	Approved
0.6146	Remote Similarity	NPD7515	Phase 2
0.6146	Remote Similarity	NPD5694	Approved
0.6129	Remote Similarity	NPD4249	Approved
0.6105	Remote Similarity	NPD1695	Approved
0.6098	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6686	Approved
0.6075	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD3573	Approved
0.6061	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD5343	Approved
0.6049	Remote Similarity	NPD7341	Phase 2
0.6042	Remote Similarity	NPD5692	Phase 3
0.6042	Remote Similarity	NPD5207	Approved
0.604	Remote Similarity	NPD7798	Approved
0.6036	Remote Similarity	NPD7641	Discontinued
0.6018	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD3174	Discontinued
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD6685	Approved
0.596	Remote Similarity	NPD5695	Phase 3
0.5957	Remote Similarity	NPD5279	Phase 3
0.5957	Remote Similarity	NPD6098	Approved
0.5943	Remote Similarity	NPD6899	Approved
0.5943	Remote Similarity	NPD6881	Approved
0.5938	Remote Similarity	NPD6080	Approved
0.5938	Remote Similarity	NPD6904	Approved
0.5938	Remote Similarity	NPD6673	Approved
0.5938	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5346	Phase 2
0.5938	Remote Similarity	NPD5347	Phase 2
0.5914	Remote Similarity	NPD4786	Approved
0.5914	Remote Similarity	NPD3668	Phase 3
0.5913	Remote Similarity	NPD7830	Approved
0.5913	Remote Similarity	NPD7829	Approved
0.5905	Remote Similarity	NPD5739	Approved
0.5905	Remote Similarity	NPD7128	Approved
0.5905	Remote Similarity	NPD6402	Approved
0.5905	Remote Similarity	NPD5048	Discontinued
0.5905	Remote Similarity	NPD6675	Approved
0.5897	Remote Similarity	NPD8074	Phase 3
0.5882	Remote Similarity	NPD6648	Approved
0.5872	Remote Similarity	NPD6882	Approved
0.587	Remote Similarity	NPD3667	Approved
0.5865	Remote Similarity	NPD5765	Approved
0.5862	Remote Similarity	NPD8341	Approved
0.5862	Remote Similarity	NPD8340	Approved
0.5862	Remote Similarity	NPD8299	Approved
0.5862	Remote Similarity	NPD8342	Approved
0.5859	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5697	Approved
0.5849	Remote Similarity	NPD6412	Phase 2
0.5833	Remote Similarity	NPD7290	Approved
0.5833	Remote Similarity	NPD7102	Approved
0.5833	Remote Similarity	NPD6883	Approved
0.5833	Remote Similarity	NPD6371	Approved
0.5816	Remote Similarity	NPD8035	Phase 2
0.5816	Remote Similarity	NPD8034	Phase 2
0.5812	Remote Similarity	NPD8451	Approved
0.5812	Remote Similarity	NPD8273	Phase 1
0.5804	Remote Similarity	NPD7500	Approved
0.58	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7320	Approved
0.5789	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5696	Approved
0.5784	Remote Similarity	NPD4225	Approved
0.578	Remote Similarity	NPD8130	Phase 1
0.578	Remote Similarity	NPD6650	Approved
0.578	Remote Similarity	NPD6869	Approved
0.578	Remote Similarity	NPD6649	Approved
0.578	Remote Similarity	NPD6617	Approved
0.578	Remote Similarity	NPD6847	Approved
0.5778	Remote Similarity	NPD4238	Approved
0.5778	Remote Similarity	NPD4802	Phase 2
0.5763	Remote Similarity	NPD8448	Approved
0.5753	Remote Similarity	NPD3173	Approved
0.5745	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD3665	Phase 1
0.5745	Remote Similarity	NPD3666	Approved
0.5745	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD3133	Approved
0.5743	Remote Similarity	NPD1989	Approved
0.5741	Remote Similarity	NPD6373	Approved
0.5741	Remote Similarity	NPD6012	Approved
0.5741	Remote Similarity	NPD6372	Approved
0.5741	Remote Similarity	NPD6013	Approved
0.5741	Remote Similarity	NPD6014	Approved
0.5729	Remote Similarity	NPD4793	Discontinued
0.5729	Remote Similarity	NPD1087	Approved
0.5727	Remote Similarity	NPD8297	Approved
0.5714	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5701	Approved
0.5698	Remote Similarity	NPD7144	Approved
0.5698	Remote Similarity	NPD7143	Approved
0.5688	Remote Similarity	NPD2067	Discontinued
0.5684	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD4058	Approved
0.5682	Remote Similarity	NPD6926	Approved
0.5682	Remote Similarity	NPD4687	Approved
0.5682	Remote Similarity	NPD6924	Approved
0.5682	Remote Similarity	NPD5733	Approved
0.5679	Remote Similarity	NPD4191	Approved
0.5679	Remote Similarity	NPD4194	Approved
0.5679	Remote Similarity	NPD4193	Approved
0.5679	Remote Similarity	NPD4192	Approved
0.567	Remote Similarity	NPD5208	Approved
0.5667	Remote Similarity	NPD6932	Approved
0.5664	Remote Similarity	NPD7115	Discovery
0.5657	Remote Similarity	NPD5693	Phase 1
0.5657	Remote Similarity	NPD6079	Approved
0.5652	Remote Similarity	NPD4695	Discontinued

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