NPASS Compound

Structure

NPC84317 OpenBabel07101718322D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 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 3.4641 -0.0000 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 2.5981 0.5000 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 -0.8660 1.5000 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 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -0.8660 0.5000 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 -0.0000 -1.0000 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 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 0.0000 -0.0000 0.0000 N 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 -2.5981 0.5000 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 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 15 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 7 1 6 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.15
Volume:	343.481
LogP:	1.195
LogD:	1.474
LogS:	-2.7
# Rotatable Bonds:	5
TPSA:	110.58
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.685
Synthetic Accessibility Score:	2.774
Fsp3:	0.333
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:	-4.763
MDCK Permeability:	3.120872497675009e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.876
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	93.0465087890625%
Volume Distribution (VD):	0.652
Pgp-substrate:	5.318645000457764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.836
CYP1A2-substrate:	0.239
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.538
CYP2C9-substrate:	0.571
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.292
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	11.197
Half-life (T1/2):	0.653

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.652
Drug-inuced Liver Injury (DILI):	0.229
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.055
Carcinogencity:	0.963
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.331

Download Data

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

Natural Product: NPC84317

Natural Product ID:	NPC84317
*Common Name:**	Aurantiomide C
IUPAC Name:	3-[(1Z,4S)-1-(2-methylpropylidene)-3,6-dioxo-4H-pyrazino[2,1-b]quinazolin-4-yl]propanamide
Synonyms:	Aurantiomide C
Standard InCHIKey:	UKYRPVOCKVERNT-XXYUJHKVSA-N
Standard InCHI:	InChI=1S/C18H20N4O3/c1-10(2)9-13-16-20-12-6-4-3-5-11(12)18(25)22(16)14(17(24)21-13)7-8-15(19)23/h3-6,9-10,14H,7-8H2,1-2H3,(H2,19,23)(H,21,24)/b13-9-/t14-/m0/s1
SMILES:	OC(=N)CC[C@H]1C(=N/C(=CC(C)C)/c2n1c(=O)c1c(n2)cccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227844
PubChem CID:	16680722
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	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	48.0	ug.mL-1	PMID[486162]
NPT27	Others	Unspecified		IC50	=	48.0	ug.mL-1	PMID[486162]

☑ 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 NPC84317 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	406
0.1-0.2	5375
0.2-0.3	15774
0.3-0.4	14599
0.4-0.5	2727
0.5-0.6	2939
0.6-0.7	737
0.7-0.8	94
0.8-0.85	34
0.85-0.9	10
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC154478
0.8246	Intermediate Similarity	NPC471195
0.8246	Intermediate Similarity	NPC471196
0.8182	Intermediate Similarity	NPC324445
0.8163	Intermediate Similarity	NPC207428
0.8086	Intermediate Similarity	NPC113056
0.8086	Intermediate Similarity	NPC138293
0.8037	Intermediate Similarity	NPC471130
0.8	Intermediate Similarity	NPC300299
0.7914	Intermediate Similarity	NPC88970
0.7895	Intermediate Similarity	NPC122553
0.787	Intermediate Similarity	NPC14849
0.7778	Intermediate Similarity	NPC106118
0.7758	Intermediate Similarity	NPC189116
0.7751	Intermediate Similarity	NPC328611
0.7742	Intermediate Similarity	NPC2823
0.7727	Intermediate Similarity	NPC83214
0.7719	Intermediate Similarity	NPC131450
0.7719	Intermediate Similarity	NPC147298
0.7719	Intermediate Similarity	NPC182057
0.7647	Intermediate Similarity	NPC248862
0.7581	Intermediate Similarity	NPC472538
0.7581	Intermediate Similarity	NPC471155
0.7569	Intermediate Similarity	NPC471199
0.754	Intermediate Similarity	NPC270241
0.7527	Intermediate Similarity	NPC225400
0.7487	Intermediate Similarity	NPC470786
0.7485	Intermediate Similarity	NPC117032
0.7452	Intermediate Similarity	NPC207554
0.7433	Intermediate Similarity	NPC471191
0.7419	Intermediate Similarity	NPC295548
0.7389	Intermediate Similarity	NPC92803
0.7382	Intermediate Similarity	NPC153980
0.7382	Intermediate Similarity	NPC6865
0.7356	Intermediate Similarity	NPC474081
0.7338	Intermediate Similarity	NPC325479
0.7333	Intermediate Similarity	NPC295021
0.733	Intermediate Similarity	NPC72956
0.7299	Intermediate Similarity	NPC475607
0.7296	Intermediate Similarity	NPC316202
0.7283	Intermediate Similarity	NPC472541
0.7283	Intermediate Similarity	NPC472542
0.7278	Intermediate Similarity	NPC18890
0.7244	Intermediate Similarity	NPC162417
0.7244	Intermediate Similarity	NPC316104
0.7241	Intermediate Similarity	NPC475594
0.7228	Intermediate Similarity	NPC472540
0.7228	Intermediate Similarity	NPC472539
0.7228	Intermediate Similarity	NPC470787
0.7225	Intermediate Similarity	NPC355
0.7216	Intermediate Similarity	NPC475761
0.7205	Intermediate Similarity	NPC314287
0.7202	Intermediate Similarity	NPC471193
0.7202	Intermediate Similarity	NPC471194
0.7194	Intermediate Similarity	NPC248601
0.7179	Intermediate Similarity	NPC471192
0.7134	Intermediate Similarity	NPC254798
0.7119	Intermediate Similarity	NPC474041
0.7118	Intermediate Similarity	NPC27904
0.7081	Intermediate Similarity	NPC198401
0.7081	Intermediate Similarity	NPC471164
0.7056	Intermediate Similarity	NPC21429
0.7024	Intermediate Similarity	NPC471132
0.7	Intermediate Similarity	NPC291962
0.7	Intermediate Similarity	NPC104345
0.7	Intermediate Similarity	NPC177684
0.6954	Remote Similarity	NPC258531
0.6954	Remote Similarity	NPC112373
0.6954	Remote Similarity	NPC161956
0.6951	Remote Similarity	NPC136002
0.6943	Remote Similarity	NPC316746
0.694	Remote Similarity	NPC473815
0.6919	Remote Similarity	NPC68650
0.6913	Remote Similarity	NPC239357
0.6908	Remote Similarity	NPC257490
0.6889	Remote Similarity	NPC475685
0.6879	Remote Similarity	NPC314431
0.6871	Remote Similarity	NPC471574
0.6867	Remote Similarity	NPC478039
0.6842	Remote Similarity	NPC279385
0.6842	Remote Similarity	NPC179605
0.6821	Remote Similarity	NPC220698
0.6818	Remote Similarity	NPC283130
0.6818	Remote Similarity	NPC328683
0.68	Remote Similarity	NPC471197
0.6797	Remote Similarity	NPC103292
0.6795	Remote Similarity	NPC322433
0.679	Remote Similarity	NPC132636
0.6779	Remote Similarity	NPC33742
0.6772	Remote Similarity	NPC472245
0.6766	Remote Similarity	NPC471198
0.6753	Remote Similarity	NPC39818
0.6739	Remote Similarity	NPC307396
0.6722	Remote Similarity	NPC471743
0.6716	Remote Similarity	NPC15384
0.6716	Remote Similarity	NPC244425
0.6709	Remote Similarity	NPC150863
0.6709	Remote Similarity	NPC111428
0.6703	Remote Similarity	NPC88110
0.6689	Remote Similarity	NPC285926
0.6689	Remote Similarity	NPC315276
0.6689	Remote Similarity	NPC14672
0.6687	Remote Similarity	NPC40364
0.6686	Remote Similarity	NPC133470
0.6686	Remote Similarity	NPC191863
0.6686	Remote Similarity	NPC237649
0.6686	Remote Similarity	NPC289776
0.6686	Remote Similarity	NPC300596
0.6685	Remote Similarity	NPC472118
0.6684	Remote Similarity	NPC16249
0.6667	Remote Similarity	NPC301760
0.6667	Remote Similarity	NPC22746
0.6667	Remote Similarity	NPC147983
0.6667	Remote Similarity	NPC177996
0.665	Remote Similarity	NPC285192
0.6648	Remote Similarity	NPC475094
0.6647	Remote Similarity	NPC172937
0.6647	Remote Similarity	NPC94167
0.6646	Remote Similarity	NPC58827
0.6646	Remote Similarity	NPC72473
0.6646	Remote Similarity	NPC307437
0.6645	Remote Similarity	NPC470545
0.6624	Remote Similarity	NPC474926
0.6624	Remote Similarity	NPC101719
0.6623	Remote Similarity	NPC200964
0.6613	Remote Similarity	NPC150308
0.6612	Remote Similarity	NPC91179
0.6606	Remote Similarity	NPC472243
0.6601	Remote Similarity	NPC470546
0.6599	Remote Similarity	NPC164802
0.6595	Remote Similarity	NPC228835
0.6581	Remote Similarity	NPC71684
0.6579	Remote Similarity	NPC470544
0.6576	Remote Similarity	NPC270301
0.6568	Remote Similarity	NPC259678
0.6566	Remote Similarity	NPC43477
0.6562	Remote Similarity	NPC226662
0.6562	Remote Similarity	NPC280807
0.6562	Remote Similarity	NPC194562
0.6561	Remote Similarity	NPC276430
0.6561	Remote Similarity	NPC222466
0.6559	Remote Similarity	NPC133003
0.6524	Remote Similarity	NPC141612
0.6524	Remote Similarity	NPC135601
0.6524	Remote Similarity	NPC17273
0.6506	Remote Similarity	NPC130251
0.6503	Remote Similarity	NPC253476
0.65	Remote Similarity	NPC473322
0.6497	Remote Similarity	NPC472117
0.649	Remote Similarity	NPC276949
0.649	Remote Similarity	NPC35850
0.6484	Remote Similarity	NPC470548
0.6484	Remote Similarity	NPC469529
0.648	Remote Similarity	NPC182131
0.6477	Remote Similarity	NPC316282
0.6474	Remote Similarity	NPC473002
0.6464	Remote Similarity	NPC318183
0.6464	Remote Similarity	NPC292265
0.6453	Remote Similarity	NPC144691
0.6441	Remote Similarity	NPC472102
0.6441	Remote Similarity	NPC309531
0.6437	Remote Similarity	NPC469903
0.6429	Remote Similarity	NPC313449
0.6429	Remote Similarity	NPC472241
0.6429	Remote Similarity	NPC471944
0.642	Remote Similarity	NPC255447
0.6419	Remote Similarity	NPC172170
0.641	Remote Similarity	NPC27833
0.6407	Remote Similarity	NPC315051
0.6405	Remote Similarity	NPC288232
0.6398	Remote Similarity	NPC313722
0.6394	Remote Similarity	NPC220851
0.6392	Remote Similarity	NPC254698
0.6392	Remote Similarity	NPC474082
0.6392	Remote Similarity	NPC175726
0.6389	Remote Similarity	NPC300631
0.6386	Remote Similarity	NPC287358
0.6384	Remote Similarity	NPC473003
0.6383	Remote Similarity	NPC476341
0.638	Remote Similarity	NPC53044
0.6379	Remote Similarity	NPC285381
0.6378	Remote Similarity	NPC11126
0.6375	Remote Similarity	NPC477937
0.6358	Remote Similarity	NPC200589
0.6354	Remote Similarity	NPC66490
0.6353	Remote Similarity	NPC314186
0.6344	Remote Similarity	NPC39822
0.6337	Remote Similarity	NPC13470
0.6331	Remote Similarity	NPC238499
0.633	Remote Similarity	NPC471742
0.633	Remote Similarity	NPC285923
0.6329	Remote Similarity	NPC268534
0.6319	Remote Similarity	NPC471943
0.6316	Remote Similarity	NPC17059
0.6316	Remote Similarity	NPC472242
0.6316	Remote Similarity	NPC311658
0.6313	Remote Similarity	NPC476231
0.6313	Remote Similarity	NPC472101
0.6313	Remote Similarity	NPC472120
0.6313	Remote Similarity	NPC472121

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 NPC84317 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	602
0.2-0.3	1015
0.3-0.4	1878
0.4-0.5	2164
0.5-0.6	2193
0.6-0.7	926
0.7-0.8	145
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
0.7962	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4942	Approved
0.7919	Intermediate Similarity	NPD1920	Approved
0.7919	Intermediate Similarity	NPD1919	Approved
0.7917	Intermediate Similarity	NPD4091	Approved
0.7904	Intermediate Similarity	NPD7443	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD5042	Phase 1
0.787	Intermediate Similarity	NPD4092	Approved
0.7778	Intermediate Similarity	NPD951	Approved
0.7765	Intermediate Similarity	NPD3991	Approved
0.7765	Intermediate Similarity	NPD3994	Approved
0.7765	Intermediate Similarity	NPD3995	Approved
0.7765	Intermediate Similarity	NPD3996	Approved
0.7765	Intermediate Similarity	NPD3992	Approved
0.7765	Intermediate Similarity	NPD3993	Approved
0.7751	Intermediate Similarity	NPD3522	Approved
0.7746	Intermediate Similarity	NPD5923	Phase 1
0.7736	Intermediate Similarity	NPD979	Approved
0.7719	Intermediate Similarity	NPD3999	Approved
0.7719	Intermediate Similarity	NPD3997	Approved
0.7719	Intermediate Similarity	NPD3998	Approved
0.7674	Intermediate Similarity	NPD3989	Phase 3
0.7633	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3990	Phase 3
0.7548	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1524	Phase 1
0.7485	Intermediate Similarity	NPD3248	Phase 1
0.7483	Intermediate Similarity	NPD1781	Discontinued
0.7469	Intermediate Similarity	NPD5748	Phase 2
0.7438	Intermediate Similarity	NPD6017	Discontinued
0.7414	Intermediate Similarity	NPD7428	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7065	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7014	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6613	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4515	Suspended
0.7215	Intermediate Similarity	NPD4214	Discontinued
0.7202	Intermediate Similarity	NPD4517	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2950	Approved
0.7179	Intermediate Similarity	NPD2949	Approved
0.7176	Intermediate Similarity	NPD4564	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4565	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4158	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4393	Approved
0.716	Intermediate Similarity	NPD33	Approved
0.7143	Intermediate Similarity	NPD6855	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7662	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7817	Phase 1
0.7124	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5423	Phase 2
0.7083	Intermediate Similarity	NPD7072	Phase 2
0.7073	Intermediate Similarity	NPD3519	Discontinued
0.707	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4412	Phase 2
0.7051	Intermediate Similarity	NPD1001	Discontinued
0.7047	Intermediate Similarity	NPD3968	Approved
0.703	Intermediate Similarity	NPD7088	Discontinued
0.702	Intermediate Similarity	NPD1123	Approved
0.702	Intermediate Similarity	NPD1079	Discontinued
0.702	Intermediate Similarity	NPD1124	Approved
0.7006	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6575	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7795	Phase 2
0.6968	Remote Similarity	NPD5856	Discontinued
0.6966	Remote Similarity	NPD5681	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3411	Phase 2
0.6943	Remote Similarity	NPD3410	Approved
0.6932	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6557	Phase 2
0.6923	Remote Similarity	NPD4549	Discontinued
0.6902	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3967	Approved
0.6886	Remote Similarity	NPD4432	Discontinued
0.6867	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD941	Approved
0.6855	Remote Similarity	NPD1541	Approved
0.6852	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7142	Discontinued
0.6852	Remote Similarity	NPD7254	Discontinued
0.6842	Remote Similarity	NPD7091	Discontinued
0.6835	Remote Similarity	NPD1619	Phase 3
0.6829	Remote Similarity	NPD6768	Approved
0.6826	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD478	Approved
0.6795	Remote Similarity	NPD9540	Approved
0.6789	Remote Similarity	NPD1991	Phase 2
0.6789	Remote Similarity	NPD1992	Phase 2
0.6789	Remote Similarity	NPD1990	Phase 2
0.6788	Remote Similarity	NPD6301	Phase 2
0.6788	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3802	Phase 3
0.6788	Remote Similarity	NPD5024	Approved
0.6778	Remote Similarity	NPD5840	Discontinued
0.6757	Remote Similarity	NPD4988	Discontinued
0.6751	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2356	Phase 1
0.6744	Remote Similarity	NPD6395	Phase 2
0.6744	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7232	Discontinued
0.673	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7600	Phase 2
0.6708	Remote Similarity	NPD5272	Discontinued
0.6707	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5510	Approved
0.6689	Remote Similarity	NPD1344	Phase 2
0.6688	Remote Similarity	NPD1593	Approved
0.6687	Remote Similarity	NPD6901	Phase 3
0.6686	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4682	Phase 2
0.6686	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2369	Discontinued
0.6685	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2791	Discontinued
0.6667	Remote Similarity	NPD7599	Phase 2
0.6667	Remote Similarity	NPD1108	Approved
0.6667	Remote Similarity	NPD8050	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3353	Approved
0.6667	Remote Similarity	NPD2010	Phase 3
0.6667	Remote Similarity	NPD1107	Approved
0.6667	Remote Similarity	NPD9541	Approved
0.6667	Remote Similarity	NPD9539	Approved
0.665	Remote Similarity	NPD6486	Approved
0.665	Remote Similarity	NPD6487	Approved
0.6649	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7572	Phase 2
0.6648	Remote Similarity	NPD7771	Discontinued
0.6647	Remote Similarity	NPD1967	Approved
0.6647	Remote Similarity	NPD2527	Approved
0.6647	Remote Similarity	NPD5918	Discontinued
0.6647	Remote Similarity	NPD1968	Approved
0.6647	Remote Similarity	NPD3016	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1527	Phase 2
0.6645	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD480	Approved
0.6633	Remote Similarity	NPD6260	Discontinued
0.6629	Remote Similarity	NPD5989	Phase 1
0.6627	Remote Similarity	NPD6088	Approved
0.6627	Remote Similarity	NPD3513	Phase 3
0.6626	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1036	Approved
0.6614	Remote Similarity	NPD7786	Discontinued
0.6605	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2659	Approved
0.66	Remote Similarity	NPD3148	Approved
0.66	Remote Similarity	NPD3149	Approved
0.66	Remote Similarity	NPD2658	Approved
0.66	Remote Similarity	NPD3147	Approved
0.66	Remote Similarity	NPD3150	Approved
0.6599	Remote Similarity	NPD2679	Approved
0.6599	Remote Similarity	NPD2678	Approved
0.6599	Remote Similarity	NPD477	Phase 1
0.6588	Remote Similarity	NPD5942	Approved
0.6588	Remote Similarity	NPD5941	Approved
0.6587	Remote Similarity	NPD2129	Approved
0.6587	Remote Similarity	NPD2820	Phase 3
0.6582	Remote Similarity	NPD8114	Approved
0.6582	Remote Similarity	NPD8115	Approved
0.6578	Remote Similarity	NPD3246	Discontinued
0.6575	Remote Similarity	NPD2461	Phase 1
0.6566	Remote Similarity	NPD7720	Phase 2
0.6564	Remote Similarity	NPD3908	Approved
0.6562	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD8240	Discontinued
0.6557	Remote Similarity	NPD3782	Discontinued
0.655	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4540	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2037	Approved
0.6534	Remote Similarity	NPD2506	Approved
0.6533	Remote Similarity	NPD1764	Approved
0.6533	Remote Similarity	NPD1762	Approved
0.6532	Remote Similarity	NPD2360	Approved
0.6529	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2365	Approved
0.6526	Remote Similarity	NPD7569	Approved
0.6526	Remote Similarity	NPD7570	Approved
0.6524	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4330	Approved
0.6522	Remote Similarity	NPD4329	Approved
0.6519	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7225	Discontinued
0.6514	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1323	Discontinued
0.6513	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7727	Phase 2
0.6509	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7483	Phase 2
0.6505	Remote Similarity	NPD7482	Phase 2
0.6495	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7308	Discontinued
0.6494	Remote Similarity	NPD7463	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