NPASS Compound

Structure

NPC255060 OpenBabel07101719142D 23 23 0 0 1 0 0 0 0 0999 V2000 -0.9271 -6.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4448 -4.2603 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 -0.2200 -5.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6766 -2.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0306 -2.8461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4177 -1.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2283 -3.8120 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 -0.4788 -4.5191 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 14 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 14 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 11 1 0 0 0 0 10 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 15 3 1 1 0 0 0 15 16 1 0 0 0 0 16 12 1 1 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 11 1 1 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.21
Volume:	347.369
LogP:	2.61
LogD:	2.956
LogS:	-2.859
# Rotatable Bonds:	9
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	4.541
Fsp3:	0.722
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.424
MDCK Permeability:	3.7528385291807353e-05
Pgp-inhibitor:	0.8
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.585
Plasma Protein Binding (PPB):	83.92691040039062%
Volume Distribution (VD):	1.508
Pgp-substrate:	8.40863037109375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.39
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.298
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.714
CYP3A4-substrate:	0.579

ADMET: Excretion

Clearance (CL):	12.738
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.459
Drug-inuced Liver Injury (DILI):	0.779
AMES Toxicity:	0.851
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.955
Carcinogencity:	0.841
Eye Corrosion:	0.821
Eye Irritation:	0.753
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC255060

Natural Product ID:	NPC255060
*Common Name:**	Manadoperoxide A
IUPAC Name:	methyl 2-[(3S,4S,6R)-6-methoxy-4-methyl-6-[(4E,6E)-6-methylocta-4,6-dienyl]dioxan-3-yl]acetate
Synonyms:
Standard InCHIKey:	SXYZFCRIZKWROR-FGLSIJRNSA-N
Standard InCHI:	InChI=1S/C18H30O5/c1-6-14(2)10-8-7-9-11-18(21-5)13-15(3)16(22-23-18)12-17(19)20-4/h6,8,10,15-16H,7,9,11-13H2,1-5H3/b10-8+,14-6+/t15-,16-,18+/m0/s1
SMILES:	C/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:	CHEMBL1164343
PubChem CID:	46850009
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	=	6880.0	nM	PMID[469776]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3740.0	nM	PMID[469776]

☑ 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 NPC255060 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	NPC239127
0.9155	High Similarity	NPC167145
0.9041	High Similarity	NPC474447
0.9041	High Similarity	NPC266119
0.9028	High Similarity	NPC330016
0.8667	High Similarity	NPC476325
0.8667	High Similarity	NPC476264
0.8571	High Similarity	NPC469920
0.8553	High Similarity	NPC121200
0.8533	High Similarity	NPC469514
0.8421	Intermediate Similarity	NPC281296
0.8378	Intermediate Similarity	NPC474543
0.8378	Intermediate Similarity	NPC238425
0.8378	Intermediate Similarity	NPC472018
0.8356	Intermediate Similarity	NPC69462
0.8267	Intermediate Similarity	NPC474551
0.825	Intermediate Similarity	NPC69469
0.8228	Intermediate Similarity	NPC475481
0.8228	Intermediate Similarity	NPC79277
0.8228	Intermediate Similarity	NPC476988
0.8219	Intermediate Similarity	NPC107130
0.8205	Intermediate Similarity	NPC308545
0.8205	Intermediate Similarity	NPC82488
0.8158	Intermediate Similarity	NPC60718
0.8108	Intermediate Similarity	NPC472017
0.8052	Intermediate Similarity	NPC476987
0.8052	Intermediate Similarity	NPC152754
0.8052	Intermediate Similarity	NPC59602
0.8	Intermediate Similarity	NPC117960
0.8	Intermediate Similarity	NPC14044
0.8	Intermediate Similarity	NPC172309
0.7975	Intermediate Similarity	NPC113363
0.7952	Intermediate Similarity	NPC477994
0.7952	Intermediate Similarity	NPC477993
0.7922	Intermediate Similarity	NPC199445
0.7867	Intermediate Similarity	NPC475310
0.7857	Intermediate Similarity	NPC86005
0.7821	Intermediate Similarity	NPC475744
0.7821	Intermediate Similarity	NPC476985
0.7821	Intermediate Similarity	NPC474316
0.7805	Intermediate Similarity	NPC475989
0.7763	Intermediate Similarity	NPC126061
0.7763	Intermediate Similarity	NPC320119
0.775	Intermediate Similarity	NPC254996
0.775	Intermediate Similarity	NPC268502
0.7738	Intermediate Similarity	NPC476104
0.7738	Intermediate Similarity	NPC476982
0.7722	Intermediate Similarity	NPC122847
0.7722	Intermediate Similarity	NPC145898
0.7674	Intermediate Similarity	NPC97577
0.7619	Intermediate Similarity	NPC474369
0.7619	Intermediate Similarity	NPC471344
0.759	Intermediate Similarity	NPC476983
0.7531	Intermediate Similarity	NPC158565
0.7531	Intermediate Similarity	NPC469747
0.7531	Intermediate Similarity	NPC263574
0.7529	Intermediate Similarity	NPC262085
0.75	Intermediate Similarity	NPC474760
0.75	Intermediate Similarity	NPC199557
0.75	Intermediate Similarity	NPC36491
0.7471	Intermediate Similarity	NPC471342
0.7471	Intermediate Similarity	NPC118193
0.7471	Intermediate Similarity	NPC256902
0.7471	Intermediate Similarity	NPC469866
0.7468	Intermediate Similarity	NPC475861
0.7465	Intermediate Similarity	NPC226602
0.7465	Intermediate Similarity	NPC472019
0.7465	Intermediate Similarity	NPC472020
0.7442	Intermediate Similarity	NPC477959
0.7439	Intermediate Similarity	NPC274522
0.7439	Intermediate Similarity	NPC476265
0.7436	Intermediate Similarity	NPC326024
0.7416	Intermediate Similarity	NPC478037
0.7416	Intermediate Similarity	NPC478036
0.7407	Intermediate Similarity	NPC470905
0.7407	Intermediate Similarity	NPC476986
0.7407	Intermediate Similarity	NPC218817
0.7407	Intermediate Similarity	NPC11796
0.7403	Intermediate Similarity	NPC472955
0.7375	Intermediate Similarity	NPC266159
0.7375	Intermediate Similarity	NPC472967
0.7363	Intermediate Similarity	NPC165332
0.7363	Intermediate Similarity	NPC195645
0.7363	Intermediate Similarity	NPC180722
0.7361	Intermediate Similarity	NPC472021
0.7356	Intermediate Similarity	NPC201046
0.7333	Intermediate Similarity	NPC284447
0.7326	Intermediate Similarity	NPC116575
0.7294	Intermediate Similarity	NPC120158
0.7294	Intermediate Similarity	NPC471343
0.7294	Intermediate Similarity	NPC475193
0.7284	Intermediate Similarity	NPC107668
0.7284	Intermediate Similarity	NPC469867
0.7284	Intermediate Similarity	NPC240170
0.7284	Intermediate Similarity	NPC120776
0.7283	Intermediate Similarity	NPC475438
0.7273	Intermediate Similarity	NPC477449
0.7273	Intermediate Similarity	NPC296522
0.7273	Intermediate Similarity	NPC144511
0.7273	Intermediate Similarity	NPC477448
0.7262	Intermediate Similarity	NPC476984
0.7262	Intermediate Similarity	NPC475395
0.7262	Intermediate Similarity	NPC85772
0.725	Intermediate Similarity	NPC324762
0.725	Intermediate Similarity	NPC228978
0.7229	Intermediate Similarity	NPC103634
0.7215	Intermediate Similarity	NPC470237
0.7215	Intermediate Similarity	NPC135703
0.7209	Intermediate Similarity	NPC76333
0.72	Intermediate Similarity	NPC318420
0.72	Intermediate Similarity	NPC326268
0.7195	Intermediate Similarity	NPC127526
0.7195	Intermediate Similarity	NPC474341
0.7191	Intermediate Similarity	NPC51653
0.7191	Intermediate Similarity	NPC313670
0.7176	Intermediate Similarity	NPC475947
0.7176	Intermediate Similarity	NPC476100
0.7176	Intermediate Similarity	NPC312480
0.7176	Intermediate Similarity	NPC16488
0.7162	Intermediate Similarity	NPC54925
0.716	Intermediate Similarity	NPC110461
0.716	Intermediate Similarity	NPC12740
0.7159	Intermediate Similarity	NPC473151
0.7143	Intermediate Similarity	NPC141810
0.7143	Intermediate Similarity	NPC473435
0.7143	Intermediate Similarity	NPC281949
0.7143	Intermediate Similarity	NPC39411
0.7143	Intermediate Similarity	NPC25684
0.7143	Intermediate Similarity	NPC5418
0.7143	Intermediate Similarity	NPC42470
0.7143	Intermediate Similarity	NPC255580
0.7143	Intermediate Similarity	NPC301477
0.7143	Intermediate Similarity	NPC228473
0.7143	Intermediate Similarity	NPC471078
0.7143	Intermediate Similarity	NPC473280
0.7143	Intermediate Similarity	NPC473431
0.7128	Intermediate Similarity	NPC469871
0.7128	Intermediate Similarity	NPC469870
0.7126	Intermediate Similarity	NPC316426
0.7126	Intermediate Similarity	NPC70422
0.7126	Intermediate Similarity	NPC234038
0.7126	Intermediate Similarity	NPC469483
0.7126	Intermediate Similarity	NPC315395
0.7126	Intermediate Similarity	NPC198314
0.7126	Intermediate Similarity	NPC70555
0.7126	Intermediate Similarity	NPC104961
0.7126	Intermediate Similarity	NPC475753
0.7125	Intermediate Similarity	NPC306928
0.7108	Intermediate Similarity	NPC63649
0.7108	Intermediate Similarity	NPC471740
0.7108	Intermediate Similarity	NPC617
0.7108	Intermediate Similarity	NPC28319
0.7108	Intermediate Similarity	NPC264227
0.7108	Intermediate Similarity	NPC472965
0.7093	Intermediate Similarity	NPC196487
0.7093	Intermediate Similarity	NPC14575
0.7093	Intermediate Similarity	NPC139566
0.7079	Intermediate Similarity	NPC115179
0.7079	Intermediate Similarity	NPC212598
0.7079	Intermediate Similarity	NPC106040
0.7073	Intermediate Similarity	NPC171204
0.7073	Intermediate Similarity	NPC470240
0.7073	Intermediate Similarity	NPC476794
0.7073	Intermediate Similarity	NPC476028
0.7073	Intermediate Similarity	NPC141789
0.7073	Intermediate Similarity	NPC97516
0.7067	Intermediate Similarity	NPC234767
0.7065	Intermediate Similarity	NPC314009
0.7065	Intermediate Similarity	NPC54905
0.7059	Intermediate Similarity	NPC474605
0.7059	Intermediate Similarity	NPC476292
0.7059	Intermediate Similarity	NPC475936
0.7051	Intermediate Similarity	NPC473772
0.7051	Intermediate Similarity	NPC329656
0.7045	Intermediate Similarity	NPC471739
0.7037	Intermediate Similarity	NPC329826
0.7037	Intermediate Similarity	NPC469414
0.7024	Intermediate Similarity	NPC233377
0.7024	Intermediate Similarity	NPC474510
0.7011	Intermediate Similarity	NPC261380
0.7	Intermediate Similarity	NPC253144
0.6989	Remote Similarity	NPC471153
0.6989	Remote Similarity	NPC151725
0.6989	Remote Similarity	NPC122324
0.6989	Remote Similarity	NPC106425
0.6988	Remote Similarity	NPC128276
0.6988	Remote Similarity	NPC4827
0.6986	Remote Similarity	NPC475821
0.6979	Remote Similarity	NPC475091
0.6977	Remote Similarity	NPC318468
0.6977	Remote Similarity	NPC170377
0.6977	Remote Similarity	NPC170286
0.6977	Remote Similarity	NPC53867
0.6977	Remote Similarity	NPC474703
0.6974	Remote Similarity	NPC215987
0.6974	Remote Similarity	NPC306805
0.6962	Remote Similarity	NPC476660
0.6957	Remote Similarity	NPC216407
0.6951	Remote Similarity	NPC301525
0.6951	Remote Similarity	NPC474527

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 NPC255060 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
0.7674	Intermediate Similarity	NPD6101	Approved
0.7674	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6411	Approved
0.7363	Intermediate Similarity	NPD7839	Suspended
0.7303	Intermediate Similarity	NPD7983	Approved
0.725	Intermediate Similarity	NPD8039	Approved
0.7222	Intermediate Similarity	NPD5778	Approved
0.7222	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD5369	Approved
0.7059	Intermediate Similarity	NPD6435	Approved
0.7024	Intermediate Similarity	NPD5368	Approved
0.6977	Remote Similarity	NPD7154	Phase 3
0.686	Remote Similarity	NPD4270	Approved
0.686	Remote Similarity	NPD5209	Approved
0.686	Remote Similarity	NPD4269	Approved
0.6813	Remote Similarity	NPD46	Approved
0.6813	Remote Similarity	NPD6698	Approved
0.6782	Remote Similarity	NPD5362	Discontinued
0.6742	Remote Similarity	NPD5786	Approved
0.6629	Remote Similarity	NPD5363	Approved
0.6628	Remote Similarity	NPD4820	Approved
0.6628	Remote Similarity	NPD4822	Approved
0.6628	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4819	Approved
0.6628	Remote Similarity	NPD4821	Approved
0.6628	Remote Similarity	NPD4252	Approved
0.6596	Remote Similarity	NPD5282	Discontinued
0.6588	Remote Similarity	NPD4268	Approved
0.6588	Remote Similarity	NPD4271	Approved
0.6588	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD28	Approved
0.6571	Remote Similarity	NPD29	Approved
0.6559	Remote Similarity	NPD7637	Suspended
0.6556	Remote Similarity	NPD6422	Discontinued
0.6526	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5785	Approved
0.641	Remote Similarity	NPD3197	Phase 1
0.6395	Remote Similarity	NPD3732	Approved
0.6389	Remote Similarity	NPD3172	Approved
0.6374	Remote Similarity	NPD7146	Approved
0.6374	Remote Similarity	NPD7521	Approved
0.6374	Remote Similarity	NPD5330	Approved
0.6374	Remote Similarity	NPD6684	Approved
0.6374	Remote Similarity	NPD7334	Approved
0.6374	Remote Similarity	NPD6409	Approved
0.6329	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6399	Phase 3
0.6301	Remote Similarity	NPD4266	Approved
0.6301	Remote Similarity	NPD3196	Approved
0.6301	Remote Similarity	NPD3195	Phase 2
0.6301	Remote Similarity	NPD3194	Approved
0.6279	Remote Similarity	NPD4756	Discovery
0.6277	Remote Similarity	NPD3673	Approved
0.6277	Remote Similarity	NPD7838	Discovery
0.6277	Remote Similarity	NPD3672	Approved
0.6264	Remote Similarity	NPD1694	Approved
0.6264	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7331	Phase 2
0.6237	Remote Similarity	NPD6903	Approved
0.6237	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6672	Approved
0.6237	Remote Similarity	NPD5737	Approved
0.6234	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5332	Approved
0.6222	Remote Similarity	NPD5331	Approved
0.6211	Remote Similarity	NPD5281	Approved
0.6211	Remote Similarity	NPD5694	Approved
0.6211	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5284	Approved
0.6203	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4249	Approved
0.618	Remote Similarity	NPD4790	Discontinued
0.617	Remote Similarity	NPD1695	Approved
0.617	Remote Similarity	NPD5370	Suspended
0.6129	Remote Similarity	NPD4251	Approved
0.6129	Remote Similarity	NPD4250	Approved
0.6129	Remote Similarity	NPD3573	Approved
0.6105	Remote Similarity	NPD5207	Approved
0.6105	Remote Similarity	NPD5692	Phase 3
0.6087	Remote Similarity	NPD3174	Discontinued
0.6087	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7748	Approved
0.6071	Remote Similarity	NPD8513	Phase 3
0.6071	Remote Similarity	NPD8516	Approved
0.6071	Remote Similarity	NPD8517	Approved
0.6071	Remote Similarity	NPD8515	Approved
0.6067	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7902	Approved
0.6049	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7515	Phase 2
0.6042	Remote Similarity	NPD6050	Approved
0.6022	Remote Similarity	NPD5279	Phase 3
0.602	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD6686	Approved
0.5981	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3668	Phase 3
0.5976	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5048	Discontinued
0.596	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7641	Discontinued
0.5941	Remote Similarity	NPD7798	Approved
0.5934	Remote Similarity	NPD3667	Approved
0.5929	Remote Similarity	NPD8444	Approved
0.5926	Remote Similarity	NPD7341	Phase 2
0.5918	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD5343	Approved
0.5905	Remote Similarity	NPD6685	Approved
0.5905	Remote Similarity	NPD5697	Approved
0.5905	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6083	Phase 2
0.59	Remote Similarity	NPD6084	Phase 2
0.5851	Remote Similarity	NPD6098	Approved
0.5849	Remote Similarity	NPD6881	Approved
0.5849	Remote Similarity	NPD6899	Approved
0.5842	Remote Similarity	NPD4225	Approved
0.5842	Remote Similarity	NPD5696	Approved
0.5833	Remote Similarity	NPD6080	Approved
0.5833	Remote Similarity	NPD3173	Approved
0.5833	Remote Similarity	NPD6673	Approved
0.5833	Remote Similarity	NPD6904	Approved
0.5833	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5346	Phase 2
0.5833	Remote Similarity	NPD5347	Phase 2
0.5826	Remote Similarity	NPD7829	Approved
0.5826	Remote Similarity	NPD7830	Approved
0.5812	Remote Similarity	NPD8074	Phase 3
0.581	Remote Similarity	NPD6402	Approved
0.581	Remote Similarity	NPD7128	Approved
0.581	Remote Similarity	NPD5739	Approved
0.581	Remote Similarity	NPD6675	Approved
0.5806	Remote Similarity	NPD4786	Approved
0.5806	Remote Similarity	NPD3666	Approved
0.5806	Remote Similarity	NPD3133	Approved
0.5806	Remote Similarity	NPD3665	Phase 1
0.58	Remote Similarity	NPD1989	Approved
0.5794	Remote Similarity	NPD6014	Approved
0.5794	Remote Similarity	NPD6013	Approved
0.5794	Remote Similarity	NPD6012	Approved
0.5789	Remote Similarity	NPD1087	Approved
0.5784	Remote Similarity	NPD6648	Approved
0.578	Remote Similarity	NPD6882	Approved
0.5776	Remote Similarity	NPD8342	Approved
0.5776	Remote Similarity	NPD8341	Approved
0.5776	Remote Similarity	NPD8299	Approved
0.5776	Remote Similarity	NPD8340	Approved
0.5769	Remote Similarity	NPD5765	Approved
0.5755	Remote Similarity	NPD6412	Phase 2
0.5755	Remote Similarity	NPD5701	Approved
0.575	Remote Similarity	NPD4191	Approved
0.575	Remote Similarity	NPD4194	Approved
0.575	Remote Similarity	NPD4192	Approved
0.575	Remote Similarity	NPD4193	Approved
0.5747	Remote Similarity	NPD4687	Approved
0.5747	Remote Similarity	NPD4058	Approved
0.5741	Remote Similarity	NPD7290	Approved
0.5741	Remote Similarity	NPD7102	Approved
0.5741	Remote Similarity	NPD6371	Approved
0.5741	Remote Similarity	NPD2067	Discontinued
0.5741	Remote Similarity	NPD6883	Approved
0.5729	Remote Similarity	NPD5208	Approved
0.5726	Remote Similarity	NPD8451	Approved
0.5726	Remote Similarity	NPD8273	Phase 1
0.5714	Remote Similarity	NPD4695	Discontinued
0.5714	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD8035	Phase 2
0.5714	Remote Similarity	NPD7500	Approved
0.5714	Remote Similarity	NPD5693	Phase 1
0.5701	Remote Similarity	NPD7320	Approved
0.5701	Remote Similarity	NPD6011	Approved
0.57	Remote Similarity	NPD5654	Approved
0.57	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD5276	Approved
0.5694	Remote Similarity	NPD622	Approved
0.5688	Remote Similarity	NPD6847	Approved
0.5688	Remote Similarity	NPD8130	Phase 1
0.5688	Remote Similarity	NPD6650	Approved
0.5688	Remote Similarity	NPD6869	Approved
0.5688	Remote Similarity	NPD6649	Approved
0.5688	Remote Similarity	NPD6617	Approved
0.5684	Remote Similarity	NPD3618	Phase 1
0.5679	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD8448	Approved
0.5676	Remote Similarity	NPD2650	Approved
0.5676	Remote Similarity	NPD2652	Approved
0.567	Remote Similarity	NPD800	Approved
0.567	Remote Similarity	NPD4753	Phase 2
0.5667	Remote Similarity	NPD225	Approved
0.5667	Remote Similarity	NPD227	Approved
0.5667	Remote Similarity	NPD4802	Phase 2
0.5667	Remote Similarity	NPD4238	Approved
0.5663	Remote Similarity	NPD3704	Approved
0.566	Remote Similarity	NPD6008	Approved
0.5658	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6372	Approved
0.5648	Remote Similarity	NPD6373	Approved
0.5638	Remote Similarity	NPD7338	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