NPASS Compound

Structure

NPC471197 OpenBabel07101719252D 38 43 0 0 1 0 0 0 0 0999 V2000 1.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0388 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -4.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5388 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5388 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 0.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 -0.4819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5388 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 -1.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0388 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5388 -2.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -2.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 -1.3660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -2.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -3.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 -3.0981 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 14 1 0 0 0 0 2 14 1 0 0 0 0 4 16 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 17 2 0 0 0 0 10 18 2 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 15 3 1 1 0 0 0 15 24 1 0 0 0 0 15 29 1 0 0 0 0 16 33 2 0 0 0 0 16 37 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 19 30 1 0 0 0 0 20 32 1 0 0 0 0 21 13 1 6 0 0 0 21 26 1 0 0 0 0 21 31 1 0 0 0 0 22 14 1 1 0 0 0 22 23 1 0 0 0 0 22 37 1 0 0 0 0 23 30 2 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 24 34 2 0 0 0 0 25 31 1 0 0 0 0 25 35 2 0 0 0 0 26 36 2 0 0 0 0 26 38 1 0 0 0 0 27 28 1 6 0 0 0 27 29 1 0 0 0 0 27 32 1 0 0 0 0 28 13 1 1 0 0 0 28 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.2
Volume:	509.233
LogP:	2.018
LogD:	1.705
LogS:	-5.146
# Rotatable Bonds:	5
TPSA:	119.83
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	4.979
Fsp3:	0.393
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.311
MDCK Permeability:	2.2955591703066602e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.725
30% Bioavailability (F30%):	0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	56.63486862182617%
Volume Distribution (VD):	0.944
Pgp-substrate:	50.987770080566406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.621
CYP2C9-inhibitor:	0.625
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.859
CYP3A4-substrate:	0.934

ADMET: Excretion

Clearance (CL):	2.526
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.987
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.126
Carcinogencity:	0.1
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.414

Download Data

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

Natural Product: NPC471197

Natural Product ID:	NPC471197
*Common Name:**	Deoxynortryptoquivaline
IUPAC Name:	[(1S)-1-[3-[(2S,3'R,3aR,4S)-2-methyl-1,2'-dioxospiro[3,3a-dihydro-2H-imidazo[1,2-a]indole-4,5'-oxolane]-3'-yl]-4-oxoquinazolin-2-yl]-2-methylpropyl] acetate
Synonyms:
Standard InCHIKey:	UQWRSTHNSHDTCA-RPNIZAGGSA-N
Standard InCHI:	InChI=1S/C28H28N4O6/c1-14(2)22(37-16(4)33)23-30-19-11-7-5-9-17(19)25(35)31(23)21-13-28(38-26(21)36)18-10-6-8-12-20(18)32-24(34)15(3)29-27(28)32/h5-12,14-15,21-22,27,29H,13H2,1-4H3/t15-,21+,22-,27+,28-/m0/s1
SMILES:	CC1C(=O)N2C(N1)C3(CC(C(=O)O3)N4C(=O)C5=CC=CC=C5N=C4C(C(C)C)OC(=O)C)C6=CC=CC=C62
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386534
PubChem CID:	71725624
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0000394] Alpha amino acid esters

*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
NPO33176	cladosporium sp.	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23758051]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	87000.0	nM	PMID[466047]

☑ 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 NPC471197 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	441
0.1-0.2	2614
0.2-0.3	12833
0.3-0.4	17585
0.4-0.5	4516
0.5-0.6	3041
0.6-0.7	1525
0.7-0.8	102
0.8-0.85	16
0.85-0.9	16
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9948	High Similarity	NPC471198
0.9492	High Similarity	NPC244425
0.9492	High Similarity	NPC15384
0.9482	High Similarity	NPC285192
0.8966	High Similarity	NPC248601
0.875	High Similarity	NPC472538
0.875	High Similarity	NPC470786
0.87	High Similarity	NPC225400
0.8657	High Similarity	NPC471155
0.8614	High Similarity	NPC270241
0.8325	Intermediate Similarity	NPC295548
0.8209	Intermediate Similarity	NPC472541
0.8209	Intermediate Similarity	NPC472542
0.8159	Intermediate Similarity	NPC472540
0.8159	Intermediate Similarity	NPC472539
0.8159	Intermediate Similarity	NPC470787
0.7951	Intermediate Similarity	NPC106118
0.7854	Intermediate Similarity	NPC471199
0.7635	Intermediate Similarity	NPC473815
0.7614	Intermediate Similarity	NPC177261
0.7476	Intermediate Similarity	NPC471196
0.7476	Intermediate Similarity	NPC471195
0.7437	Intermediate Similarity	NPC285622
0.7413	Intermediate Similarity	NPC474081
0.7376	Intermediate Similarity	NPC475761
0.7363	Intermediate Similarity	NPC475607
0.7313	Intermediate Similarity	NPC475594
0.731	Intermediate Similarity	NPC189116
0.73	Intermediate Similarity	NPC355
0.7282	Intermediate Similarity	NPC307396
0.7255	Intermediate Similarity	NPC475685
0.7251	Intermediate Similarity	NPC198401
0.7228	Intermediate Similarity	NPC470548
0.7208	Intermediate Similarity	NPC68650
0.7207	Intermediate Similarity	NPC477979
0.7206	Intermediate Similarity	NPC474041
0.7202	Intermediate Similarity	NPC243850
0.7198	Intermediate Similarity	NPC322621
0.7109	Intermediate Similarity	NPC276430
0.7073	Intermediate Similarity	NPC186669
0.7048	Intermediate Similarity	NPC272174
0.7018	Intermediate Similarity	NPC471436
0.7015	Intermediate Similarity	NPC471130
0.7	Intermediate Similarity	NPC473615
0.6985	Remote Similarity	NPC154478
0.6967	Remote Similarity	NPC14994
0.6967	Remote Similarity	NPC229484
0.6965	Remote Similarity	NPC113056
0.6965	Remote Similarity	NPC138293
0.6957	Remote Similarity	NPC321211
0.6955	Remote Similarity	NPC14812
0.6954	Remote Similarity	NPC295021
0.6952	Remote Similarity	NPC259626
0.6948	Remote Similarity	NPC25401
0.6943	Remote Similarity	NPC474896
0.6934	Remote Similarity	NPC292675
0.6933	Remote Similarity	NPC54744
0.6926	Remote Similarity	NPC122886
0.6915	Remote Similarity	NPC293458
0.6915	Remote Similarity	NPC88970
0.6913	Remote Similarity	NPC31097
0.6912	Remote Similarity	NPC472118
0.6912	Remote Similarity	NPC100863
0.691	Remote Similarity	NPC471762
0.6905	Remote Similarity	NPC97584
0.6905	Remote Similarity	NPC2933
0.6897	Remote Similarity	NPC279527
0.6897	Remote Similarity	NPC214960
0.6875	Remote Similarity	NPC475094
0.6872	Remote Similarity	NPC471192
0.6872	Remote Similarity	NPC36405
0.6867	Remote Similarity	NPC257851
0.6867	Remote Similarity	NPC157931
0.6858	Remote Similarity	NPC471663
0.6857	Remote Similarity	NPC159963
0.6857	Remote Similarity	NPC256288
0.685	Remote Similarity	NPC123241
0.6847	Remote Similarity	NPC277350
0.6833	Remote Similarity	NPC477179
0.6829	Remote Similarity	NPC314882
0.6827	Remote Similarity	NPC14849
0.6822	Remote Similarity	NPC89987
0.6818	Remote Similarity	NPC471944
0.6814	Remote Similarity	NPC153980
0.6814	Remote Similarity	NPC471193
0.6814	Remote Similarity	NPC6865
0.6814	Remote Similarity	NPC471194
0.6802	Remote Similarity	NPC477178
0.6802	Remote Similarity	NPC477180
0.6802	Remote Similarity	NPC477181
0.6802	Remote Similarity	NPC254850
0.68	Remote Similarity	NPC84317
0.6794	Remote Similarity	NPC182057
0.6794	Remote Similarity	NPC147298
0.6794	Remote Similarity	NPC131450
0.6786	Remote Similarity	NPC471950
0.6786	Remote Similarity	NPC471945
0.6781	Remote Similarity	NPC115588
0.6779	Remote Similarity	NPC264482
0.6779	Remote Similarity	NPC203202
0.6771	Remote Similarity	NPC471191
0.6771	Remote Similarity	NPC477173
0.6771	Remote Similarity	NPC477174
0.6771	Remote Similarity	NPC470490
0.677	Remote Similarity	NPC72956
0.6766	Remote Similarity	NPC66777
0.6766	Remote Similarity	NPC194740
0.6762	Remote Similarity	NPC472999
0.6756	Remote Similarity	NPC471946
0.6756	Remote Similarity	NPC471951
0.6754	Remote Similarity	NPC478157
0.6741	Remote Similarity	NPC470488
0.6735	Remote Similarity	NPC324445
0.6733	Remote Similarity	NPC193410
0.6733	Remote Similarity	NPC276085
0.6732	Remote Similarity	NPC472115
0.6732	Remote Similarity	NPC472114
0.6731	Remote Similarity	NPC328611
0.6726	Remote Similarity	NPC132539
0.6726	Remote Similarity	NPC191817
0.6726	Remote Similarity	NPC475359
0.6714	Remote Similarity	NPC6974
0.6713	Remote Similarity	NPC22476
0.6713	Remote Similarity	NPC92803
0.6711	Remote Similarity	NPC475259
0.6711	Remote Similarity	NPC470491
0.67	Remote Similarity	NPC248117
0.6699	Remote Similarity	NPC224970
0.6699	Remote Similarity	NPC167724
0.6699	Remote Similarity	NPC223595
0.6698	Remote Similarity	NPC314659
0.6697	Remote Similarity	NPC214428
0.6696	Remote Similarity	NPC312645
0.6684	Remote Similarity	NPC207554
0.6683	Remote Similarity	NPC61013
0.6683	Remote Similarity	NPC222029
0.6681	Remote Similarity	NPC478158
0.6667	Remote Similarity	NPC77777
0.6667	Remote Similarity	NPC64216
0.6667	Remote Similarity	NPC478075
0.6667	Remote Similarity	NPC242000
0.6667	Remote Similarity	NPC473298
0.6653	Remote Similarity	NPC478006
0.6652	Remote Similarity	NPC473376
0.6652	Remote Similarity	NPC123839
0.6651	Remote Similarity	NPC181928
0.6651	Remote Similarity	NPC197335
0.6651	Remote Similarity	NPC248862
0.665	Remote Similarity	NPC471122
0.665	Remote Similarity	NPC117032
0.6638	Remote Similarity	NPC219397
0.6637	Remote Similarity	NPC71238
0.6636	Remote Similarity	NPC203628
0.6635	Remote Similarity	NPC99043
0.6635	Remote Similarity	NPC218594
0.6633	Remote Similarity	NPC473329
0.662	Remote Similarity	NPC18890
0.6618	Remote Similarity	NPC472102
0.6618	Remote Similarity	NPC309531
0.6617	Remote Similarity	NPC469903
0.6612	Remote Similarity	NPC151171
0.6605	Remote Similarity	NPC150308
0.6602	Remote Similarity	NPC471124
0.66	Remote Similarity	NPC303374
0.6594	Remote Similarity	NPC118940
0.6592	Remote Similarity	NPC232600
0.6591	Remote Similarity	NPC245916
0.659	Remote Similarity	NPC5630
0.6585	Remote Similarity	NPC286871
0.6578	Remote Similarity	NPC87714
0.6574	Remote Similarity	NPC94862
0.6569	Remote Similarity	NPC469902
0.6569	Remote Similarity	NPC469901
0.6565	Remote Similarity	NPC89508
0.6564	Remote Similarity	NPC266249
0.6562	Remote Similarity	NPC300299
0.6562	Remote Similarity	NPC315467
0.6562	Remote Similarity	NPC173295
0.6558	Remote Similarity	NPC49184
0.655	Remote Similarity	NPC54981
0.6545	Remote Similarity	NPC34717
0.6542	Remote Similarity	NPC139373
0.654	Remote Similarity	NPC24370
0.654	Remote Similarity	NPC319232
0.6537	Remote Similarity	NPC314817
0.6537	Remote Similarity	NPC316297
0.6537	Remote Similarity	NPC66191
0.6531	Remote Similarity	NPC243782
0.6529	Remote Similarity	NPC154922
0.6527	Remote Similarity	NPC223242
0.6524	Remote Similarity	NPC303658
0.6524	Remote Similarity	NPC242269
0.6523	Remote Similarity	NPC314056
0.652	Remote Similarity	NPC113946
0.6517	Remote Similarity	NPC314223
0.6516	Remote Similarity	NPC303214
0.6516	Remote Similarity	NPC472293
0.6515	Remote Similarity	NPC284888
0.6514	Remote Similarity	NPC61332
0.6514	Remote Similarity	NPC240130

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 NPC471197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	571
0.2-0.3	866
0.3-0.4	1693
0.4-0.5	2519
0.5-0.6	2072
0.6-0.7	1099
0.7-0.8	101
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
0.7783	Intermediate Similarity	NPD5042	Phase 1
0.7711	Intermediate Similarity	NPD6557	Phase 2
0.7463	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5856	Discontinued
0.7277	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD8240	Discontinued
0.7069	Intermediate Similarity	NPD7688	Phase 1
0.7061	Intermediate Similarity	NPD8311	Discontinued
0.7005	Intermediate Similarity	NPD3989	Phase 3
0.6995	Remote Similarity	NPD7569	Approved
0.6995	Remote Similarity	NPD7570	Approved
0.6971	Remote Similarity	NPD3990	Phase 3
0.697	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4515	Suspended
0.6953	Remote Similarity	NPD6199	Discontinued
0.6944	Remote Similarity	NPD5515	Phase 2
0.6927	Remote Similarity	NPD5997	Discontinued
0.6898	Remote Similarity	NPD3964	Approved
0.6884	Remote Similarity	NPD1059	Phase 2
0.6878	Remote Similarity	NPD3947	Discontinued
0.6864	Remote Similarity	NPD6532	Discontinued
0.6861	Remote Similarity	NPD2509	Approved
0.6861	Remote Similarity	NPD2510	Approved
0.686	Remote Similarity	NPD4091	Approved
0.6849	Remote Similarity	NPD6805	Discontinued
0.6844	Remote Similarity	NPD7470	Discontinued
0.6833	Remote Similarity	NPD3802	Phase 3
0.6827	Remote Similarity	NPD4092	Approved
0.6827	Remote Similarity	NPD3992	Approved
0.6827	Remote Similarity	NPD3994	Approved
0.6827	Remote Similarity	NPD3996	Approved
0.6827	Remote Similarity	NPD3991	Approved
0.6827	Remote Similarity	NPD3993	Approved
0.6827	Remote Similarity	NPD3995	Approved
0.6822	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6238	Discontinued
0.6802	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3999	Approved
0.6794	Remote Similarity	NPD3998	Approved
0.6794	Remote Similarity	NPD3997	Approved
0.6786	Remote Similarity	NPD1801	Approved
0.6786	Remote Similarity	NPD1802	Approved
0.6786	Remote Similarity	NPD7232	Discontinued
0.6783	Remote Similarity	NPD6770	Approved
0.6765	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6878	Phase 2
0.6762	Remote Similarity	NPD6879	Phase 2
0.6758	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD5941	Approved
0.6751	Remote Similarity	NPD5942	Approved
0.6746	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD5923	Phase 1
0.6742	Remote Similarity	NPD7817	Phase 1
0.674	Remote Similarity	NPD7225	Discontinued
0.6731	Remote Similarity	NPD3522	Approved
0.6731	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4982	Discontinued
0.6725	Remote Similarity	NPD3394	Approved
0.6725	Remote Similarity	NPD3389	Approved
0.6725	Remote Similarity	NPD3393	Approved
0.6725	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4301	Approved
0.6716	Remote Similarity	NPD7105	Phase 1
0.6711	Remote Similarity	NPD6487	Approved
0.6711	Remote Similarity	NPD4356	Discontinued
0.6711	Remote Similarity	NPD6486	Approved
0.6709	Remote Similarity	NPD3441	Approved
0.6709	Remote Similarity	NPD3442	Approved
0.6698	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6218	Discontinued
0.6682	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6176	Phase 1
0.668	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6752	Phase 1
0.6667	Remote Similarity	NPD7605	Discovery
0.6667	Remote Similarity	NPD7853	Phase 2
0.6667	Remote Similarity	NPD7398	Approved
0.6667	Remote Similarity	NPD3371	Approved
0.6667	Remote Similarity	NPD7397	Approved
0.6667	Remote Similarity	NPD6753	Phase 1
0.6667	Remote Similarity	NPD1623	Approved
0.665	Remote Similarity	NPD3248	Phase 1
0.665	Remote Similarity	NPD7599	Phase 2
0.6639	Remote Similarity	NPD4946	Phase 2
0.6636	Remote Similarity	NPD5076	Approved
0.6636	Remote Similarity	NPD5077	Approved
0.6635	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6995	Phase 1
0.6623	Remote Similarity	NPD3915	Approved
0.6623	Remote Similarity	NPD2813	Phase 3
0.6623	Remote Similarity	NPD1591	Approved
0.6623	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6519	Phase 2
0.662	Remote Similarity	NPD5851	Approved
0.662	Remote Similarity	NPD5852	Approved
0.6617	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7205	Discontinued
0.6607	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7573	Discontinued
0.6594	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD3918	Approved
0.6594	Remote Similarity	NPD3917	Approved
0.6583	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4154	Approved
0.6564	Remote Similarity	NPD4082	Approved
0.6561	Remote Similarity	NPD7572	Phase 2
0.6556	Remote Similarity	NPD6142	Phase 3
0.6556	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5475	Discontinued
0.6544	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.654	Remote Similarity	NPD8289	Discontinued
0.6537	Remote Similarity	NPD7600	Phase 2
0.6533	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4492	Approved
0.6522	Remote Similarity	NPD4494	Approved
0.652	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7560	Approved
0.6513	Remote Similarity	NPD7994	Phase 2
0.6509	Remote Similarity	NPD6596	Phase 2
0.6509	Remote Similarity	NPD1960	Phase 2
0.6507	Remote Similarity	NPD5186	Approved
0.6507	Remote Similarity	NPD5183	Approved
0.6502	Remote Similarity	NPD7072	Phase 2
0.65	Remote Similarity	NPD7528	Approved
0.6493	Remote Similarity	NPD5466	Approved
0.6491	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3775	Approved
0.6489	Remote Similarity	NPD3774	Approved
0.6489	Remote Similarity	NPD3773	Approved
0.6486	Remote Similarity	NPD3828	Approved
0.6484	Remote Similarity	NPD6659	Phase 2
0.6482	Remote Similarity	NPD7776	Approved
0.6481	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4493	Discontinued
0.6476	Remote Similarity	NPD6260	Discontinued
0.6475	Remote Similarity	NPD7677	Discontinued
0.6471	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD951	Approved
0.6468	Remote Similarity	NPD1996	Discontinued
0.6468	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5293	Phase 2
0.6466	Remote Similarity	NPD4558	Phase 2
0.6463	Remote Similarity	NPD4506	Discontinued
0.6463	Remote Similarity	NPD3592	Approved
0.6463	Remote Similarity	NPD3874	Discontinued
0.6463	Remote Similarity	NPD3591	Approved
0.6461	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD2893	Phase 3
0.6449	Remote Similarity	NPD5445	Approved
0.6447	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7727	Phase 2
0.6444	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6321	Discontinued
0.6444	Remote Similarity	NPD5552	Discontinued
0.6439	Remote Similarity	NPD8630	Approved
0.6438	Remote Similarity	NPD3353	Approved
0.6438	Remote Similarity	NPD8160	Phase 2
0.6435	Remote Similarity	NPD4412	Phase 2
0.6432	Remote Similarity	NPD8115	Approved
0.6432	Remote Similarity	NPD8114	Approved
0.6432	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD5116	Phase 1
0.6429	Remote Similarity	NPD6249	Phase 2
0.6429	Remote Similarity	NPD6248	Phase 2
0.6429	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6891	Phase 2
0.6416	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD8162	Phase 2
0.6415	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5024	Approved
0.6413	Remote Similarity	NPD5003	Discontinued
0.641	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4938	Phase 2
0.6406	Remote Similarity	NPD1920	Approved
0.6406	Remote Similarity	NPD1919	Approved
0.6404	Remote Similarity	NPD4130	Phase 3
0.6404	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7010	Phase 3
0.6402	Remote Similarity	NPD7186	Phase 3
0.6402	Remote Similarity	NPD7775	Approved
0.64	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3437	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data