NPASS Compound

Structure

NPC154478 OpenBabel07101719522D 26 28 0 0 1 0 0 0 0 0999 V2000 1.3837 2.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2894 2.8801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 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 0.1589 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4177 2.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 0.8660 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 N 0 0 0 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 1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7899 0.8827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 11 2 0 0 0 0 6 12 2 0 0 0 0 7 8 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 20 1 0 0 0 0 13 7 1 1 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 21 2 0 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 16 25 2 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 21 1 0 0 0 0 18 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.16
Volume:	354.908
LogP:	0.728
LogD:	0.681
LogS:	-3.123
# Rotatable Bonds:	5
TPSA:	127.31
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	3.746
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.088
MDCK Permeability:	1.4980017112975474e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.14

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.879
Plasma Protein Binding (PPB):	64.19859313964844%
Volume Distribution (VD):	0.658
Pgp-substrate:	39.065189361572266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.141
CYP2C9-substrate:	0.609
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	6.331
Half-life (T1/2):	0.342

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.269
Drug-inuced Liver Injury (DILI):	0.723
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.286
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.066
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.191

Download Data

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

Natural Product: NPC154478

Natural Product ID:	NPC154478
*Common Name:**	Aurantiomide B
IUPAC Name:	3-[(1R,4S)-1-hydroxy-1-(2-methylpropyl)-3,6-dioxo-2,4-dihydropyrazino[2,1-b]quinazolin-4-yl]propanamide
Synonyms:
Standard InCHIKey:	VZHFOIYILDANRZ-SCLBCKFNSA-N
Standard InCHI:	InChI=1S/C18H22N4O4/c1-10(2)9-18(26)17-20-12-6-4-3-5-11(12)16(25)22(17)13(15(24)21-18)7-8-14(19)23/h3-6,10,13,26H,7-9H2,1-2H3,(H2,19,23)(H,21,24)/t13-,18+/m0/s1
SMILES:	CC(C[C@]1(O)N=C(O)[C@@H](n2c1nc1ccccc1c2=O)CCC(=N)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227765
PubChem CID:	16680721
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*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
NPO32728	penicillium aurantiogriseum sp0-19	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17455978]

☑ 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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	52.0	ug.mL-1	PMID[541323]
NPT168	Cell Line	P388	Mus musculus	IC50	=	54.0	ug.mL-1	PMID[541323]

☑ 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 NPC154478 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	378
0.1-0.2	4624
0.2-0.3	15636
0.3-0.4	15399
0.4-0.5	2735
0.5-0.6	3041
0.6-0.7	745
0.7-0.8	92
0.8-0.85	38
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC84317
0.8471	Intermediate Similarity	NPC471196
0.8471	Intermediate Similarity	NPC471195
0.8312	Intermediate Similarity	NPC324445
0.8098	Intermediate Similarity	NPC138293
0.8098	Intermediate Similarity	NPC113056
0.8054	Intermediate Similarity	NPC207428
0.7895	Intermediate Similarity	NPC300299
0.7831	Intermediate Similarity	NPC471130
0.7792	Intermediate Similarity	NPC122553
0.7778	Intermediate Similarity	NPC14849
0.7771	Intermediate Similarity	NPC189116
0.7711	Intermediate Similarity	NPC88970
0.7692	Intermediate Similarity	NPC106118
0.7688	Intermediate Similarity	NPC470786
0.7688	Intermediate Similarity	NPC472538
0.7661	Intermediate Similarity	NPC328611
0.7634	Intermediate Similarity	NPC225400
0.763	Intermediate Similarity	NPC182057
0.763	Intermediate Similarity	NPC147298
0.763	Intermediate Similarity	NPC131450
0.7628	Intermediate Similarity	NPC83214
0.7594	Intermediate Similarity	NPC471155
0.7558	Intermediate Similarity	NPC248862
0.7553	Intermediate Similarity	NPC270241
0.7532	Intermediate Similarity	NPC2823
0.7527	Intermediate Similarity	NPC295548
0.7486	Intermediate Similarity	NPC471199
0.7471	Intermediate Similarity	NPC474081
0.7468	Intermediate Similarity	NPC207554
0.7421	Intermediate Similarity	NPC316202
0.7414	Intermediate Similarity	NPC475607
0.7391	Intermediate Similarity	NPC472541
0.7391	Intermediate Similarity	NPC472542
0.7385	Intermediate Similarity	NPC248601
0.7356	Intermediate Similarity	NPC475594
0.7337	Intermediate Similarity	NPC470787
0.7337	Intermediate Similarity	NPC472540
0.7337	Intermediate Similarity	NPC472539
0.733	Intermediate Similarity	NPC475761
0.7329	Intermediate Similarity	NPC314287
0.7308	Intermediate Similarity	NPC92803
0.7289	Intermediate Similarity	NPC117032
0.7263	Intermediate Similarity	NPC471191
0.7246	Intermediate Similarity	NPC295021
0.7244	Intermediate Similarity	NPC325479
0.7232	Intermediate Similarity	NPC474041
0.7216	Intermediate Similarity	NPC153980
0.7216	Intermediate Similarity	NPC6865
0.7198	Intermediate Similarity	NPC18890
0.7165	Intermediate Similarity	NPC72956
0.7152	Intermediate Similarity	NPC162417
0.7152	Intermediate Similarity	NPC316104
0.7143	Intermediate Similarity	NPC473815
0.7143	Intermediate Similarity	NPC355
0.7107	Intermediate Similarity	NPC471192
0.7099	Intermediate Similarity	NPC471164
0.7097	Intermediate Similarity	NPC198401
0.7048	Intermediate Similarity	NPC254798
0.7041	Intermediate Similarity	NPC471193
0.7041	Intermediate Similarity	NPC471194
0.7035	Intermediate Similarity	NPC27904
0.702	Intermediate Similarity	NPC177684
0.702	Intermediate Similarity	NPC291962
0.7	Intermediate Similarity	NPC475685
0.6985	Remote Similarity	NPC471197
0.6974	Remote Similarity	NPC161956
0.6974	Remote Similarity	NPC258531
0.6974	Remote Similarity	NPC112373
0.6962	Remote Similarity	NPC316746
0.695	Remote Similarity	NPC471198
0.6948	Remote Similarity	NPC328683
0.6948	Remote Similarity	NPC283130
0.6933	Remote Similarity	NPC239357
0.6928	Remote Similarity	NPC257490
0.6919	Remote Similarity	NPC104345
0.69	Remote Similarity	NPC244425
0.69	Remote Similarity	NPC15384
0.6899	Remote Similarity	NPC314431
0.6886	Remote Similarity	NPC478039
0.6885	Remote Similarity	NPC21429
0.6867	Remote Similarity	NPC136002
0.6863	Remote Similarity	NPC279385
0.6863	Remote Similarity	NPC179605
0.686	Remote Similarity	NPC94167
0.686	Remote Similarity	NPC172937
0.6842	Remote Similarity	NPC471132
0.6839	Remote Similarity	NPC68650
0.6818	Remote Similarity	NPC103292
0.681	Remote Similarity	NPC132636
0.6788	Remote Similarity	NPC471574
0.6774	Remote Similarity	NPC39818
0.6758	Remote Similarity	NPC475094
0.6757	Remote Similarity	NPC307396
0.6751	Remote Similarity	NPC285192
0.673	Remote Similarity	NPC111428
0.6709	Remote Similarity	NPC322433
0.6705	Remote Similarity	NPC191863
0.6705	Remote Similarity	NPC289776
0.6705	Remote Similarity	NPC133470
0.6704	Remote Similarity	NPC472118
0.6701	Remote Similarity	NPC16249
0.6689	Remote Similarity	NPC33742
0.6688	Remote Similarity	NPC22746
0.6687	Remote Similarity	NPC472245
0.6686	Remote Similarity	NPC259678
0.6683	Remote Similarity	NPC147983
0.6683	Remote Similarity	NPC177996
0.6667	Remote Similarity	NPC72473
0.6667	Remote Similarity	NPC307437
0.6667	Remote Similarity	NPC470545
0.6667	Remote Similarity	NPC58827
0.6648	Remote Similarity	NPC471743
0.6646	Remote Similarity	NPC101719
0.6645	Remote Similarity	NPC200964
0.6631	Remote Similarity	NPC150308
0.6625	Remote Similarity	NPC150863
0.6623	Remote Similarity	NPC470546
0.6623	Remote Similarity	NPC220698
0.6608	Remote Similarity	NPC300596
0.6608	Remote Similarity	NPC237649
0.6605	Remote Similarity	NPC40364
0.6601	Remote Similarity	NPC315276
0.6601	Remote Similarity	NPC285926
0.6601	Remote Similarity	NPC470544
0.6601	Remote Similarity	NPC14672
0.6595	Remote Similarity	NPC270301
0.6592	Remote Similarity	NPC300631
0.6587	Remote Similarity	NPC301760
0.6587	Remote Similarity	NPC43477
0.6584	Remote Similarity	NPC194562
0.6582	Remote Similarity	NPC222466
0.6579	Remote Similarity	NPC276430
0.6541	Remote Similarity	NPC88110
0.6541	Remote Similarity	NPC474926
0.6538	Remote Similarity	NPC27833
0.6527	Remote Similarity	NPC472243
0.6522	Remote Similarity	NPC473322
0.6517	Remote Similarity	NPC472117
0.651	Remote Similarity	NPC164802
0.6503	Remote Similarity	NPC470548
0.65	Remote Similarity	NPC182131
0.6497	Remote Similarity	NPC71684
0.6495	Remote Similarity	NPC316282
0.6494	Remote Similarity	NPC473002
0.6484	Remote Similarity	NPC318183
0.6484	Remote Similarity	NPC292265
0.6481	Remote Similarity	NPC280807
0.6481	Remote Similarity	NPC226662
0.6474	Remote Similarity	NPC144691
0.6464	Remote Similarity	NPC66490
0.6461	Remote Similarity	NPC309531
0.6461	Remote Similarity	NPC472102
0.6457	Remote Similarity	NPC469903
0.6452	Remote Similarity	NPC39822
0.6452	Remote Similarity	NPC91179
0.645	Remote Similarity	NPC52748
0.6443	Remote Similarity	NPC172170
0.6442	Remote Similarity	NPC255447
0.6436	Remote Similarity	NPC228835
0.6429	Remote Similarity	NPC315051
0.6429	Remote Similarity	NPC130251
0.6424	Remote Similarity	NPC253476
0.642	Remote Similarity	NPC313722
0.6415	Remote Similarity	NPC175726
0.6415	Remote Similarity	NPC254698
0.6415	Remote Similarity	NPC474082
0.6413	Remote Similarity	NPC469529
0.6407	Remote Similarity	NPC287358
0.6405	Remote Similarity	NPC276949
0.6405	Remote Similarity	NPC35850
0.6404	Remote Similarity	NPC473003
0.6402	Remote Similarity	NPC133003
0.6398	Remote Similarity	NPC477937
0.638	Remote Similarity	NPC200589
0.6374	Remote Similarity	NPC314186
0.6369	Remote Similarity	NPC181527
0.6368	Remote Similarity	NPC141612
0.6368	Remote Similarity	NPC17273
0.6368	Remote Similarity	NPC135601
0.6358	Remote Similarity	NPC13470
0.6353	Remote Similarity	NPC472241
0.6352	Remote Similarity	NPC268534
0.6337	Remote Similarity	NPC472242
0.6333	Remote Similarity	NPC220851
0.6333	Remote Similarity	NPC472101
0.6333	Remote Similarity	NPC472120
0.6333	Remote Similarity	NPC472121
0.6319	Remote Similarity	NPC209389
0.6319	Remote Similarity	NPC214960
0.6319	Remote Similarity	NPC279527
0.6316	Remote Similarity	NPC201244
0.6316	Remote Similarity	NPC478040
0.6316	Remote Similarity	NPC476341
0.6316	Remote Similarity	NPC308197
0.6316	Remote Similarity	NPC477217
0.6313	Remote Similarity	NPC469901
0.6313	Remote Similarity	NPC469902
0.6312	Remote Similarity	NPC6975
0.6307	Remote Similarity	NPC285381

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 NPC154478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	602
0.2-0.3	993
0.3-0.4	1860
0.4-0.5	2198
0.5-0.6	2228
0.6-0.7	929
0.7-0.8	132
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7975	Intermediate Similarity	NPD4942	Approved
0.7862	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4091	Approved
0.7815	Intermediate Similarity	NPD1920	Approved
0.7815	Intermediate Similarity	NPD1919	Approved
0.7811	Intermediate Similarity	NPD7443	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD5042	Phase 1
0.7791	Intermediate Similarity	NPD951	Approved
0.7778	Intermediate Similarity	NPD4092	Approved
0.7674	Intermediate Similarity	NPD3991	Approved
0.7674	Intermediate Similarity	NPD3996	Approved
0.7674	Intermediate Similarity	NPD3992	Approved
0.7674	Intermediate Similarity	NPD3994	Approved
0.7674	Intermediate Similarity	NPD3993	Approved
0.7674	Intermediate Similarity	NPD3995	Approved
0.7661	Intermediate Similarity	NPD3522	Approved
0.764	Intermediate Similarity	NPD979	Approved
0.763	Intermediate Similarity	NPD3998	Approved
0.763	Intermediate Similarity	NPD3997	Approved
0.763	Intermediate Similarity	NPD3999	Approved
0.7586	Intermediate Similarity	NPD3989	Phase 3
0.7557	Intermediate Similarity	NPD5923	Phase 1
0.7543	Intermediate Similarity	NPD3990	Phase 3
0.7452	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1781	Discontinued
0.7378	Intermediate Similarity	NPD5748	Phase 2
0.7346	Intermediate Similarity	NPD6017	Discontinued
0.733	Intermediate Similarity	NPD7428	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1524	Phase 1
0.7296	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3248	Phase 1
0.7257	Intermediate Similarity	NPD6613	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4515	Suspended
0.7191	Intermediate Similarity	NPD7014	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4393	Approved
0.7176	Intermediate Similarity	NPD33	Approved
0.7175	Intermediate Similarity	NPD7065	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7817	Phase 1
0.7125	Intermediate Similarity	NPD4214	Discontinued
0.7118	Intermediate Similarity	NPD4517	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4565	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4564	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2950	Approved
0.7089	Intermediate Similarity	NPD2949	Approved
0.7081	Intermediate Similarity	NPD4158	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5681	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7662	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6855	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7088	Discontinued
0.7032	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7072	Phase 2
0.6989	Remote Similarity	NPD7795	Phase 2
0.6988	Remote Similarity	NPD3519	Discontinued
0.6981	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3802	Phase 3
0.6978	Remote Similarity	NPD4412	Phase 2
0.6974	Remote Similarity	NPD3968	Approved
0.6949	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD478	Approved
0.6946	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6557	Phase 2
0.6928	Remote Similarity	NPD1124	Approved
0.6928	Remote Similarity	NPD1123	Approved
0.6928	Remote Similarity	NPD1079	Discontinued
0.6919	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4432	Discontinued
0.6905	Remote Similarity	NPD5423	Phase 2
0.6895	Remote Similarity	NPD5856	Discontinued
0.6875	Remote Similarity	NPD941	Approved
0.6875	Remote Similarity	NPD1541	Approved
0.6872	Remote Similarity	NPD3411	Phase 2
0.6872	Remote Similarity	NPD3410	Approved
0.6871	Remote Similarity	NPD7142	Discontinued
0.6864	Remote Similarity	NPD2356	Phase 1
0.686	Remote Similarity	NPD2527	Approved
0.6855	Remote Similarity	NPD1001	Discontinued
0.6835	Remote Similarity	NPD4549	Discontinued
0.6824	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3967	Approved
0.6807	Remote Similarity	NPD5024	Approved
0.6806	Remote Similarity	NPD1992	Phase 2
0.6806	Remote Similarity	NPD1991	Phase 2
0.6806	Remote Similarity	NPD1990	Phase 2
0.6802	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5840	Discontinued
0.6788	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7254	Discontinued
0.6763	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7091	Discontinued
0.6763	Remote Similarity	NPD6395	Phase 2
0.6751	Remote Similarity	NPD7232	Discontinued
0.675	Remote Similarity	NPD1619	Phase 3
0.675	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6768	Approved
0.6744	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7600	Phase 2
0.6735	Remote Similarity	NPD6260	Discontinued
0.6728	Remote Similarity	NPD5272	Discontinued
0.6709	Remote Similarity	NPD9540	Approved
0.6709	Remote Similarity	NPD1593	Approved
0.6707	Remote Similarity	NPD6301	Phase 2
0.6707	Remote Similarity	NPD6901	Phase 3
0.6706	Remote Similarity	NPD4682	Phase 2
0.6704	Remote Similarity	NPD2369	Discontinued
0.6703	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2791	Discontinued
0.6686	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7599	Phase 2
0.6684	Remote Similarity	NPD4988	Discontinued
0.6683	Remote Similarity	NPD3353	Approved
0.6683	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5918	Discontinued
0.6667	Remote Similarity	NPD6487	Approved
0.6667	Remote Similarity	NPD7771	Discontinued
0.6667	Remote Similarity	NPD6486	Approved
0.6667	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1967	Approved
0.6667	Remote Similarity	NPD1527	Phase 2
0.6667	Remote Similarity	NPD1968	Approved
0.6633	Remote Similarity	NPD5510	Approved
0.6627	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3626	Phase 3
0.6608	Remote Similarity	NPD5941	Approved
0.6608	Remote Similarity	NPD5942	Approved
0.6607	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1344	Phase 2
0.6599	Remote Similarity	NPD8114	Approved
0.6599	Remote Similarity	NPD8115	Approved
0.6592	Remote Similarity	NPD2546	Approved
0.6592	Remote Similarity	NPD2545	Approved
0.6587	Remote Similarity	NPD2010	Phase 3
0.6585	Remote Similarity	NPD3908	Approved
0.6584	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD9539	Approved
0.6582	Remote Similarity	NPD9541	Approved
0.6579	Remote Similarity	NPD8240	Discontinued
0.6577	Remote Similarity	NPD1107	Approved
0.6577	Remote Similarity	NPD1108	Approved
0.6576	Remote Similarity	NPD3782	Discontinued
0.6571	Remote Similarity	NPD1663	Discontinued
0.6568	Remote Similarity	NPD3016	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4540	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD480	Approved
0.6556	Remote Similarity	NPD2037	Approved
0.6554	Remote Similarity	NPD2506	Approved
0.6552	Remote Similarity	NPD2360	Approved
0.655	Remote Similarity	NPD6088	Approved
0.655	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3513	Phase 3
0.6545	Remote Similarity	NPD7786	Discontinued
0.6545	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4330	Approved
0.6541	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4329	Approved
0.6541	Remote Similarity	NPD1036	Approved
0.6531	Remote Similarity	NPD7727	Phase 2
0.6529	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD8050	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD3149	Approved
0.6513	Remote Similarity	NPD3147	Approved
0.6513	Remote Similarity	NPD2659	Approved
0.6513	Remote Similarity	NPD3148	Approved
0.6513	Remote Similarity	NPD3150	Approved
0.6513	Remote Similarity	NPD2658	Approved
0.651	Remote Similarity	NPD2678	Approved
0.651	Remote Similarity	NPD477	Phase 1
0.651	Remote Similarity	NPD2679	Approved
0.6509	Remote Similarity	NPD2129	Approved
0.6509	Remote Similarity	NPD7552	Discontinued
0.6509	Remote Similarity	NPD4430	Phase 2
0.6509	Remote Similarity	NPD2820	Phase 3
0.6508	Remote Similarity	NPD3246	Discontinued
0.6503	Remote Similarity	NPD2461	Phase 1
0.6495	Remote Similarity	NPD5515	Phase 2
0.6495	Remote Similarity	NPD7572	Phase 2
0.6492	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7720	Phase 2
0.6484	Remote Similarity	NPD2432	Approved
0.6484	Remote Similarity	NPD2431	Approved
0.648	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5593	Approved
0.6468	Remote Similarity	NPD5594	Approved
0.6467	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4167	Phase 3
0.6464	Remote Similarity	NPD2455	Approved
0.6464	Remote Similarity	NPD2454	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data