NPASS Compound

Structure

NPC155792 OpenBabel07101718302D 32 33 0 0 1 0 0 0 0 0999 V2000 1.4650 -11.2629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6557 -9.7794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7591 -6.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2074 -8.1063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4309 -11.0041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3449 -5.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6378 -4.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0860 -5.9850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8966 -3.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5050 -1.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3710 -0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6390 -1.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5050 0.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9826 -9.3311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5343 -7.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6897 -10.0382 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7932 -6.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2414 -8.3652 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3710 -1.1895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1895 -2.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 -1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4142 -1.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6390 -0.1895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2370 -1.6895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -2.8978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1213 -2.1213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -1.2247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7695 0.8020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 3 18 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 9 2 0 0 0 0 8 18 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 26 1 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 2 1 6 0 0 0 19 4 1 6 0 0 0 20 28 1 6 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 29 2 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 24 30 1 0 0 0 0 25 27 2 0 0 0 0 25 31 1 0 0 0 0 26 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	443.27
Volume:	477.632
LogP:	3.361
LogD:	1.893
LogS:	-4.191
# Rotatable Bonds:	9
TPSA:	110.62
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	4.286
Fsp3:	0.538
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:	-4.974
MDCK Permeability:	1.137384333560476e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.198
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.383

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	93.893310546875%
Volume Distribution (VD):	0.701
Pgp-substrate:	8.382352828979492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.611
CYP1A2-substrate:	0.628
CYP2C19-inhibitor:	0.771
CYP2C19-substrate:	0.187
CYP2C9-inhibitor:	0.907
CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.945
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.881
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	2.084
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.424
Drug-inuced Liver Injury (DILI):	0.485
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.664
Carcinogencity:	0.155
Eye Corrosion:	0.004
Eye Irritation:	0.129
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC155792

Natural Product ID:	NPC155792
*Common Name:**	N-Deoxymilitarinone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CFXXFGCOVLKQAW-FOBKFMRFSA-N
Standard InCHI:	InChI=1S/C26H37NO5/c1-5-17(2)14-19(4)15-18(3)8-6-7-9-22(29)23-24(30)21(16-27-25(23)31)26(32)12-10-20(28)11-13-26/h6-9,15-17,19-20,28,32H,5,10-14H2,1-4H3,(H2,27,30,31)/b8-6+,9-7+,18-15+/t17-,19-,20-,26+/m1/s1
SMILES:	CC[C@@H](C)C[C@@H](C)/C=C(C)/C=C/C=C/C(=O)c1c(c(cnc1O)[C@@]1(CC[C@H](CC1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481849
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO32517	paecilomyces farinosus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16562854]
NPO32517	paecilomyces farinosus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19670877]

☑ 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
Others	8

Activity Type	# Activity
Cell Line	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	51.0	%	PMID[485811]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	88.0	%	PMID[485811]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	21.0	%	PMID[485811]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	49.0	%	PMID[485811]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	30.0	%	PMID[485811]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	12.0	%	PMID[485811]
NPT27	Others	Unspecified		Activity	=	22.0	%	PMID[485811]

☑ 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 NPC155792 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	316
0.1-0.2	1370
0.2-0.3	5703
0.3-0.4	11799
0.4-0.5	12145
0.5-0.6	10198
0.6-0.7	931
0.7-0.8	217
0.8-0.85	8
0.85-0.9	5
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9016	High Similarity	NPC56170
0.8889	High Similarity	NPC253314
0.8021	Intermediate Similarity	NPC164340
0.7969	Intermediate Similarity	NPC44354
0.7794	Intermediate Similarity	NPC472752
0.7723	Intermediate Similarity	NPC317572
0.7688	Intermediate Similarity	NPC108469
0.7677	Intermediate Similarity	NPC146724
0.7628	Intermediate Similarity	NPC475601
0.7604	Intermediate Similarity	NPC96801
0.7604	Intermediate Similarity	NPC150698
0.7596	Intermediate Similarity	NPC476467
0.7569	Intermediate Similarity	NPC469748
0.7546	Intermediate Similarity	NPC211920
0.7546	Intermediate Similarity	NPC124029
0.7536	Intermediate Similarity	NPC475408
0.7536	Intermediate Similarity	NPC471016
0.7536	Intermediate Similarity	NPC471014
0.7535	Intermediate Similarity	NPC233727
0.7512	Intermediate Similarity	NPC329024
0.7512	Intermediate Similarity	NPC111732
0.75	Intermediate Similarity	NPC187494
0.7488	Intermediate Similarity	NPC470306
0.7488	Intermediate Similarity	NPC63041
0.7488	Intermediate Similarity	NPC477910
0.7488	Intermediate Similarity	NPC62844
0.7488	Intermediate Similarity	NPC470190
0.7488	Intermediate Similarity	NPC193361
0.7487	Intermediate Similarity	NPC473057
0.7465	Intermediate Similarity	NPC216428
0.7465	Intermediate Similarity	NPC301368
0.7465	Intermediate Similarity	NPC84815
0.7454	Intermediate Similarity	NPC328154
0.7454	Intermediate Similarity	NPC477902
0.7452	Intermediate Similarity	NPC304179
0.7452	Intermediate Similarity	NPC48042
0.7452	Intermediate Similarity	NPC472550
0.7443	Intermediate Similarity	NPC477906
0.7441	Intermediate Similarity	NPC264674
0.7434	Intermediate Similarity	NPC107123
0.7429	Intermediate Similarity	NPC472553
0.7421	Intermediate Similarity	NPC35208
0.7418	Intermediate Similarity	NPC62367
0.7418	Intermediate Similarity	NPC294579
0.7418	Intermediate Similarity	NPC144779
0.7407	Intermediate Similarity	NPC471980
0.7406	Intermediate Similarity	NPC477909
0.7406	Intermediate Similarity	NPC477907
0.7406	Intermediate Similarity	NPC42678
0.7406	Intermediate Similarity	NPC30570
0.7395	Intermediate Similarity	NPC477912
0.7391	Intermediate Similarity	NPC471015
0.7389	Intermediate Similarity	NPC320748
0.7389	Intermediate Similarity	NPC317672
0.7389	Intermediate Similarity	NPC59033
0.7389	Intermediate Similarity	NPC324245
0.7385	Intermediate Similarity	NPC285411
0.7385	Intermediate Similarity	NPC14116
0.7381	Intermediate Similarity	NPC470189
0.7381	Intermediate Similarity	NPC40919
0.7376	Intermediate Similarity	NPC238278
0.7376	Intermediate Similarity	NPC473053
0.7373	Intermediate Similarity	NPC475498
0.7373	Intermediate Similarity	NPC473850
0.7373	Intermediate Similarity	NPC475137
0.7371	Intermediate Similarity	NPC6981
0.7366	Intermediate Similarity	NPC32451
0.7366	Intermediate Similarity	NPC328559
0.7361	Intermediate Similarity	NPC127026
0.7361	Intermediate Similarity	NPC127720
0.7358	Intermediate Similarity	NPC4421
0.7358	Intermediate Similarity	NPC228331
0.7352	Intermediate Similarity	NPC311196
0.7352	Intermediate Similarity	NPC134384
0.7346	Intermediate Similarity	NPC292517
0.7343	Intermediate Similarity	NPC25442
0.7343	Intermediate Similarity	NPC12944
0.7342	Intermediate Similarity	NPC475426
0.7339	Intermediate Similarity	NPC473506
0.7336	Intermediate Similarity	NPC134637
0.7333	Intermediate Similarity	NPC52831
0.7333	Intermediate Similarity	NPC325705
0.7327	Intermediate Similarity	NPC76565
0.7327	Intermediate Similarity	NPC57797
0.7327	Intermediate Similarity	NPC250807
0.7326	Intermediate Similarity	NPC113812
0.7324	Intermediate Similarity	NPC207531
0.7317	Intermediate Similarity	NPC79223
0.7313	Intermediate Similarity	NPC180668
0.7313	Intermediate Similarity	NPC471448
0.7313	Intermediate Similarity	NPC471013
0.7313	Intermediate Similarity	NPC148896
0.7294	Intermediate Similarity	NPC26881
0.7289	Intermediate Similarity	NPC253482
0.7277	Intermediate Similarity	NPC319128
0.7273	Intermediate Similarity	NPC475644
0.7273	Intermediate Similarity	NPC471190
0.7273	Intermediate Similarity	NPC471977
0.7273	Intermediate Similarity	NPC475362
0.7273	Intermediate Similarity	NPC470486
0.7273	Intermediate Similarity	NPC156044
0.7269	Intermediate Similarity	NPC477901
0.7264	Intermediate Similarity	NPC280473
0.7264	Intermediate Similarity	NPC323551
0.726	Intermediate Similarity	NPC148860
0.7256	Intermediate Similarity	NPC473089
0.7256	Intermediate Similarity	NPC158020
0.7256	Intermediate Similarity	NPC6576
0.7256	Intermediate Similarity	NPC212768
0.7256	Intermediate Similarity	NPC75600
0.7256	Intermediate Similarity	NPC473115
0.7256	Intermediate Similarity	NPC319556
0.7249	Intermediate Similarity	NPC324619
0.7249	Intermediate Similarity	NPC475315
0.7245	Intermediate Similarity	NPC471997
0.7235	Intermediate Similarity	NPC477903
0.723	Intermediate Similarity	NPC51008
0.723	Intermediate Similarity	NPC41724
0.7227	Intermediate Similarity	NPC146824
0.7227	Intermediate Similarity	NPC87152
0.7227	Intermediate Similarity	NPC475600
0.7227	Intermediate Similarity	NPC328186
0.7227	Intermediate Similarity	NPC228377
0.7227	Intermediate Similarity	NPC122968
0.7227	Intermediate Similarity	NPC477787
0.7227	Intermediate Similarity	NPC476110
0.7227	Intermediate Similarity	NPC475631
0.7222	Intermediate Similarity	NPC472555
0.7222	Intermediate Similarity	NPC207851
0.7209	Intermediate Similarity	NPC477908
0.7209	Intermediate Similarity	NPC162812
0.7209	Intermediate Similarity	NPC206343
0.7208	Intermediate Similarity	NPC470474
0.7205	Intermediate Similarity	NPC475533
0.7202	Intermediate Similarity	NPC477911
0.7202	Intermediate Similarity	NPC235364
0.7193	Intermediate Similarity	NPC475648
0.7192	Intermediate Similarity	NPC289786
0.7186	Intermediate Similarity	NPC10904
0.7177	Intermediate Similarity	NPC289086
0.7175	Intermediate Similarity	NPC30456
0.7175	Intermediate Similarity	NPC213143
0.7171	Intermediate Similarity	NPC90229
0.7162	Intermediate Similarity	NPC91125
0.7161	Intermediate Similarity	NPC473833
0.7157	Intermediate Similarity	NPC271792
0.7143	Intermediate Similarity	NPC237702
0.7136	Intermediate Similarity	NPC477899
0.7136	Intermediate Similarity	NPC477900
0.713	Intermediate Similarity	NPC475596
0.713	Intermediate Similarity	NPC292416
0.713	Intermediate Similarity	NPC316841
0.713	Intermediate Similarity	NPC473689
0.713	Intermediate Similarity	NPC475303
0.7123	Intermediate Similarity	NPC477788
0.7114	Intermediate Similarity	NPC36498
0.7111	Intermediate Similarity	NPC170751
0.7103	Intermediate Similarity	NPC219087
0.7101	Intermediate Similarity	NPC471978
0.71	Intermediate Similarity	NPC295158
0.7098	Intermediate Similarity	NPC244839
0.7098	Intermediate Similarity	NPC320324
0.7098	Intermediate Similarity	NPC319880
0.7094	Intermediate Similarity	NPC114974
0.7064	Intermediate Similarity	NPC53255
0.7064	Intermediate Similarity	NPC478045
0.7064	Intermediate Similarity	NPC475301
0.7064	Intermediate Similarity	NPC326930
0.7064	Intermediate Similarity	NPC85879
0.7062	Intermediate Similarity	NPC309498
0.7035	Intermediate Similarity	NPC327769
0.7035	Intermediate Similarity	NPC475406
0.7034	Intermediate Similarity	NPC13603
0.7031	Intermediate Similarity	NPC119134
0.7028	Intermediate Similarity	NPC183777
0.7028	Intermediate Similarity	NPC475835
0.7028	Intermediate Similarity	NPC193238
0.7018	Intermediate Similarity	NPC314270
0.7011	Intermediate Similarity	NPC471598
0.7009	Intermediate Similarity	NPC309845
0.7004	Intermediate Similarity	NPC38959
0.7004	Intermediate Similarity	NPC477549
0.7004	Intermediate Similarity	NPC327904
0.6995	Remote Similarity	NPC171787
0.6991	Remote Similarity	NPC165837
0.6986	Remote Similarity	NPC74360
0.6985	Remote Similarity	NPC298320
0.6985	Remote Similarity	NPC317010
0.6978	Remote Similarity	NPC316065
0.6978	Remote Similarity	NPC289905
0.6971	Remote Similarity	NPC472284
0.6965	Remote Similarity	NPC320394
0.6964	Remote Similarity	NPC246381
0.6955	Remote Similarity	NPC469439
0.6955	Remote Similarity	NPC276657
0.6946	Remote Similarity	NPC206186
0.6944	Remote Similarity	NPC110182
0.6942	Remote Similarity	NPC471979
0.6935	Remote Similarity	NPC67659
0.6923	Remote Similarity	NPC473814

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 NPC155792 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	571
0.2-0.3	740
0.3-0.4	1738
0.4-0.5	3460
0.5-0.6	2029
0.6-0.7	392
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
0.7455	Intermediate Similarity	NPD1483	Discontinued
0.7371	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9510	Approved
0.7186	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9364	Phase 2
0.7114	Intermediate Similarity	NPD9363	Approved
0.7105	Intermediate Similarity	NPD2511	Approved
0.7073	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3925	Approved
0.7056	Intermediate Similarity	NPD6642	Approved
0.7056	Intermediate Similarity	NPD6641	Approved
0.7031	Intermediate Similarity	NPD5088	Discontinued
0.7026	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.695	Remote Similarity	NPD9362	Approved
0.693	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2336	Approved
0.6911	Remote Similarity	NPD9382	Approved
0.6911	Remote Similarity	NPD9383	Approved
0.6882	Remote Similarity	NPD9075	Approved
0.6882	Remote Similarity	NPD9074	Approved
0.6864	Remote Similarity	NPD1926	Approved
0.686	Remote Similarity	NPD6361	Phase 2
0.682	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7777	Approved
0.681	Remote Similarity	NPD7778	Approved
0.681	Remote Similarity	NPD6790	Phase 1
0.681	Remote Similarity	NPD53	Approved
0.6802	Remote Similarity	NPD8479	Phase 2
0.6794	Remote Similarity	NPD2307	Discontinued
0.6789	Remote Similarity	NPD7069	Discontinued
0.6787	Remote Similarity	NPD7878	Phase 2
0.6786	Remote Similarity	NPD2803	Discontinued
0.6767	Remote Similarity	NPD7886	Phase 2
0.6767	Remote Similarity	NPD7885	Phase 2
0.6751	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD820	Phase 3
0.6729	Remote Similarity	NPD5513	Phase 2
0.6725	Remote Similarity	NPD7031	Phase 1
0.6715	Remote Similarity	NPD3321	Discontinued
0.6698	Remote Similarity	NPD2831	Approved
0.6696	Remote Similarity	NPD4086	Phase 1
0.6696	Remote Similarity	NPD4845	Discontinued
0.6682	Remote Similarity	NPD1229	Phase 2
0.6667	Remote Similarity	NPD4989	Phase 2
0.6667	Remote Similarity	NPD107	Approved
0.6667	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6529	Discontinued
0.665	Remote Similarity	NPD1643	Phase 3
0.6638	Remote Similarity	NPD3006	Discontinued
0.6632	Remote Similarity	NPD9271	Approved
0.6621	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7396	Approved
0.6618	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3794	Approved
0.6606	Remote Similarity	NPD3795	Approved
0.6601	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8356	Approved
0.6591	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD2781	Approved
0.658	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5640	Discontinued
0.6571	Remote Similarity	NPD5937	Approved
0.657	Remote Similarity	NPD4375	Approved
0.6566	Remote Similarity	NPD2782	Approved
0.6566	Remote Similarity	NPD2780	Approved
0.6565	Remote Similarity	NPD5022	Discontinued
0.6565	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4429	Discontinued
0.6562	Remote Similarity	NPD6198	Phase 1
0.6549	Remote Similarity	NPD4923	Phase 1
0.6545	Remote Similarity	NPD1270	Approved
0.6538	Remote Similarity	NPD4948	Discontinued
0.6537	Remote Similarity	NPD3386	Phase 2
0.6529	Remote Similarity	NPD8370	Discontinued
0.6528	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD8325	Phase 3
0.6518	Remote Similarity	NPD8326	Phase 3
0.6518	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD2123	Phase 3
0.6516	Remote Similarity	NPD8091	Phase 3
0.6512	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4369	Phase 2
0.6493	Remote Similarity	NPD6665	Discontinued
0.6486	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD925	Approved
0.6482	Remote Similarity	NPD926	Approved
0.6478	Remote Similarity	NPD8430	Approved
0.6476	Remote Similarity	NPD1213	Phase 3
0.6474	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3813	Approved
0.6473	Remote Similarity	NPD1096	Discontinued
0.6471	Remote Similarity	NPD2896	Discontinued
0.6468	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD3947	Discontinued
0.6467	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD4551	Phase 2
0.6455	Remote Similarity	NPD2510	Approved
0.6455	Remote Similarity	NPD7467	Discontinued
0.6455	Remote Similarity	NPD2509	Approved
0.6455	Remote Similarity	NPD6376	Discontinued
0.6442	Remote Similarity	NPD4889	Approved
0.6441	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6026	Approved
0.6429	Remote Similarity	NPD4021	Phase 2
0.6425	Remote Similarity	NPD4437	Phase 3
0.6417	Remote Similarity	NPD8468	Phase 2
0.6416	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3394	Approved
0.64	Remote Similarity	NPD3393	Approved
0.64	Remote Similarity	NPD3389	Approved
0.6398	Remote Similarity	NPD8063	Discontinued
0.6393	Remote Similarity	NPD4033	Approved
0.6393	Remote Similarity	NPD4039	Approved
0.6393	Remote Similarity	NPD4038	Approved
0.6393	Remote Similarity	NPD4037	Approved
0.6393	Remote Similarity	NPD4036	Approved
0.6393	Remote Similarity	NPD4122	Approved
0.6393	Remote Similarity	NPD31	Approved
0.6393	Remote Similarity	NPD4034	Approved
0.6393	Remote Similarity	NPD4035	Approved
0.6393	Remote Similarity	NPD32	Approved
0.639	Remote Similarity	NPD6020	Phase 2
0.6389	Remote Similarity	NPD6874	Approved
0.6388	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD2899	Discontinued
0.6381	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD3178	Discontinued
0.6371	Remote Similarity	NPD6825	Phase 1
0.6364	Remote Similarity	NPD5255	Approved
0.6364	Remote Similarity	NPD7603	Discontinued
0.6364	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.636	Remote Similarity	NPD3280	Approved
0.6359	Remote Similarity	NPD484	Approved
0.6347	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD4668	Phase 2
0.6338	Remote Similarity	NPD6569	Phase 2
0.6338	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD4376	Phase 3
0.6337	Remote Similarity	NPD3986	Discontinued
0.6336	Remote Similarity	NPD3259	Approved
0.6332	Remote Similarity	NPD6298	Discontinued
0.6329	Remote Similarity	NPD5897	Approved
0.6329	Remote Similarity	NPD5899	Approved
0.6329	Remote Similarity	NPD5898	Approved
0.6325	Remote Similarity	NPD6962	Phase 2
0.6324	Remote Similarity	NPD43	Approved
0.6324	Remote Similarity	NPD6182	Approved
0.6324	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6276	Discontinued
0.632	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5901	Discontinued
0.6318	Remote Similarity	NPD7417	Discontinued
0.6318	Remote Similarity	NPD6987	Phase 1
0.6316	Remote Similarity	NPD721	Approved
0.6313	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6999	Discontinued
0.6309	Remote Similarity	NPD2761	Approved
0.6308	Remote Similarity	NPD1173	Approved
0.6303	Remote Similarity	NPD8021	Approved
0.6303	Remote Similarity	NPD8020	Approved
0.6301	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7948	Phase 1
0.6296	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD4417	Approved
0.6293	Remote Similarity	NPD7426	Phase 1
0.6293	Remote Similarity	NPD3263	Phase 3
0.629	Remote Similarity	NPD7010	Phase 3
0.629	Remote Similarity	NPD7001	Phase 3
0.6288	Remote Similarity	NPD6242	Discontinued
0.6287	Remote Similarity	NPD424	Approved
0.6287	Remote Similarity	NPD425	Approved
0.6284	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5293	Phase 2
0.6279	Remote Similarity	NPD3396	Approved
0.6279	Remote Similarity	NPD3395	Approved
0.6271	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4373	Phase 2
0.6269	Remote Similarity	NPD6635	Approved
0.6262	Remote Similarity	NPD3922	Approved
0.6262	Remote Similarity	NPD3923	Approved
0.6262	Remote Similarity	NPD3921	Approved
0.6262	Remote Similarity	NPD3924	Approved
0.6262	Remote Similarity	NPD5100	Phase 3
0.6256	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD3315	Phase 3
0.625	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD9506	Approved
0.624	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD2175	Phase 3

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