NPASS Compound

Structure

NPC471198 OpenBabel07101719252D 39 44 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 4.5388 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -4.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -4.5962 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 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 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 -0.9511 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.6180 0.0000 C 0 0 0 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 4.0388 -1.3660 0.0000 N 0 0 0 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 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 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 -1.7601 -3.8968 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 17 2 0 0 0 0 11 18 2 0 0 0 0 12 19 2 0 0 0 0 13 20 2 0 0 0 0 16 34 2 0 0 0 0 16 38 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 33 1 0 0 0 0 21 14 1 6 0 0 0 21 25 1 0 0 0 0 21 32 1 0 0 0 0 22 15 1 1 0 0 0 22 23 1 0 0 0 0 22 38 1 0 0 0 0 23 30 2 0 0 0 0 23 32 1 0 0 0 0 24 32 1 0 0 0 0 24 35 2 0 0 0 0 25 36 2 0 0 0 0 25 39 1 0 0 0 0 26 29 1 6 0 0 0 26 31 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 33 1 0 0 0 0 27 37 2 0 0 0 0 28 31 1 0 0 0 0 29 14 1 1 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.22
Volume:	526.529
LogP:	2.466
LogD:	1.977
LogS:	-5.522
# 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:	0.511
Synthetic Accessibility Score:	4.948
Fsp3:	0.414
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:	-5.262
MDCK Permeability:	2.945170854218304e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.206
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	60.695091247558594%
Volume Distribution (VD):	1.043
Pgp-substrate:	50.838829040527344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.354
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.875
CYP2C9-substrate:	0.15
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.868
CYP3A4-substrate:	0.945

ADMET: Excretion

Clearance (CL):	2.609
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.172
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.165
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.29

Download Data

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

Natural Product: NPC471198

Natural Product ID:	NPC471198
*Common Name:**	Deoxytryptoquivaline
IUPAC Name:	[(1S)-1-[3-[(3'R,3aR,4S)-2,2-dimethyl-1,2'-dioxospiro[3,3a-dihydroimidazo[1,2-a]indole-4,5'-oxolane]-3'-yl]-4-oxoquinazolin-2-yl]-2-methylpropyl] acetate
Synonyms:
Standard InCHIKey:	IMOPNDYCCIZBPJ-STOWFVKWSA-N
Standard InCHI:	InChI=1S/C29H30N4O6/c1-15(2)22(38-16(3)34)23-30-19-12-8-6-10-17(19)24(35)32(23)21-14-29(39-25(21)36)18-11-7-9-13-20(18)33-26(29)31-28(4,5)27(33)37/h6-13,15,21-22,26,31H,14H2,1-5H3/t21-,22+,26-,29+/m1/s1
SMILES:	CC(=O)O[C@H](c1nc2ccccc2c(=O)n1[C@@H]1C[C@@]2(OC1=O)[C@@H]1NC(C(=O)N1c1c2cccc1)(C)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386535
PubChem CID:	71725699
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]
NPO40616	Aspergillus sp. HNMF114	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31823605]

☑ 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	=	85000.0	nM	PMID[491755]

☑ 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 NPC471198 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	452
0.1-0.2	2643
0.2-0.3	12968
0.3-0.4	17552
0.4-0.5	4418
0.5-0.6	3057
0.6-0.7	1473
0.7-0.8	95
0.8-0.85	15
0.85-0.9	17
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9948	High Similarity	NPC471197
0.9543	High Similarity	NPC15384
0.9543	High Similarity	NPC244425
0.9433	High Similarity	NPC285192
0.8922	High Similarity	NPC248601
0.8706	High Similarity	NPC470786
0.8706	High Similarity	NPC472538
0.8663	High Similarity	NPC270241
0.8657	High Similarity	NPC225400
0.8614	High Similarity	NPC471155
0.8284	Intermediate Similarity	NPC295548
0.8168	Intermediate Similarity	NPC472541
0.8168	Intermediate Similarity	NPC472542
0.8119	Intermediate Similarity	NPC472540
0.8119	Intermediate Similarity	NPC472539
0.8119	Intermediate Similarity	NPC470787
0.8	Intermediate Similarity	NPC106118
0.7816	Intermediate Similarity	NPC471199
0.7598	Intermediate Similarity	NPC473815
0.7576	Intermediate Similarity	NPC177261
0.744	Intermediate Similarity	NPC471196
0.744	Intermediate Similarity	NPC471195
0.74	Intermediate Similarity	NPC285622
0.7376	Intermediate Similarity	NPC474081
0.734	Intermediate Similarity	NPC475761
0.7327	Intermediate Similarity	NPC475607
0.7277	Intermediate Similarity	NPC475594
0.7273	Intermediate Similarity	NPC189116
0.7264	Intermediate Similarity	NPC355
0.7246	Intermediate Similarity	NPC307396
0.7246	Intermediate Similarity	NPC322621
0.722	Intermediate Similarity	NPC475685
0.7217	Intermediate Similarity	NPC198401
0.7192	Intermediate Similarity	NPC470548
0.7175	Intermediate Similarity	NPC477979
0.7172	Intermediate Similarity	NPC68650
0.7171	Intermediate Similarity	NPC474041
0.7169	Intermediate Similarity	NPC243850
0.7075	Intermediate Similarity	NPC276430
0.7064	Intermediate Similarity	NPC471436
0.7039	Intermediate Similarity	NPC186669
0.7018	Intermediate Similarity	NPC272174
0.7005	Intermediate Similarity	NPC321211
0.6996	Remote Similarity	NPC14812
0.698	Remote Similarity	NPC471130
0.697	Remote Similarity	NPC122886
0.6967	Remote Similarity	NPC473615
0.6961	Remote Similarity	NPC472118
0.6957	Remote Similarity	NPC31097
0.695	Remote Similarity	NPC154478
0.6934	Remote Similarity	NPC229484
0.6934	Remote Similarity	NPC14994
0.6931	Remote Similarity	NPC138293
0.6931	Remote Similarity	NPC113056
0.6919	Remote Similarity	NPC259626
0.6919	Remote Similarity	NPC295021
0.6916	Remote Similarity	NPC25401
0.6913	Remote Similarity	NPC474896
0.6903	Remote Similarity	NPC54744
0.6901	Remote Similarity	NPC292675
0.6881	Remote Similarity	NPC293458
0.6881	Remote Similarity	NPC100863
0.6881	Remote Similarity	NPC88970
0.688	Remote Similarity	NPC471762
0.6872	Remote Similarity	NPC2933
0.6872	Remote Similarity	NPC97584
0.6863	Remote Similarity	NPC214960
0.6863	Remote Similarity	NPC279527
0.6842	Remote Similarity	NPC471192
0.6842	Remote Similarity	NPC36405
0.6842	Remote Similarity	NPC475094
0.6838	Remote Similarity	NPC257851
0.6838	Remote Similarity	NPC157931
0.6828	Remote Similarity	NPC471663
0.6825	Remote Similarity	NPC256288
0.6825	Remote Similarity	NPC159963
0.6816	Remote Similarity	NPC123241
0.6816	Remote Similarity	NPC277350
0.6802	Remote Similarity	NPC477179
0.6802	Remote Similarity	NPC314882
0.6794	Remote Similarity	NPC14849
0.6793	Remote Similarity	NPC89987
0.6787	Remote Similarity	NPC471944
0.6784	Remote Similarity	NPC153980
0.6784	Remote Similarity	NPC6865
0.6784	Remote Similarity	NPC471194
0.6784	Remote Similarity	NPC471193
0.6771	Remote Similarity	NPC477181
0.6771	Remote Similarity	NPC254850
0.6771	Remote Similarity	NPC477180
0.6771	Remote Similarity	NPC477178
0.6766	Remote Similarity	NPC84317
0.6762	Remote Similarity	NPC147298
0.6762	Remote Similarity	NPC182057
0.6762	Remote Similarity	NPC131450
0.6756	Remote Similarity	NPC471950
0.6756	Remote Similarity	NPC471945
0.6752	Remote Similarity	NPC115588
0.6746	Remote Similarity	NPC264482
0.6746	Remote Similarity	NPC203202
0.6741	Remote Similarity	NPC471191
0.6741	Remote Similarity	NPC470490
0.6741	Remote Similarity	NPC477173
0.6741	Remote Similarity	NPC477174
0.674	Remote Similarity	NPC72956
0.6737	Remote Similarity	NPC194740
0.6737	Remote Similarity	NPC66777
0.673	Remote Similarity	NPC472999
0.6726	Remote Similarity	NPC471946
0.6726	Remote Similarity	NPC471951
0.6725	Remote Similarity	NPC478157
0.6711	Remote Similarity	NPC470488
0.6711	Remote Similarity	NPC478075
0.6701	Remote Similarity	NPC324445
0.67	Remote Similarity	NPC276085
0.67	Remote Similarity	NPC193410
0.6699	Remote Similarity	NPC472115
0.6699	Remote Similarity	NPC328611
0.6699	Remote Similarity	NPC472114
0.6696	Remote Similarity	NPC191817
0.6696	Remote Similarity	NPC132539
0.6696	Remote Similarity	NPC475359
0.6682	Remote Similarity	NPC22476
0.6682	Remote Similarity	NPC92803
0.6682	Remote Similarity	NPC6974
0.6681	Remote Similarity	NPC470491
0.6681	Remote Similarity	NPC475259
0.6667	Remote Similarity	NPC167724
0.6667	Remote Similarity	NPC223595
0.6667	Remote Similarity	NPC314659
0.6667	Remote Similarity	NPC248117
0.6667	Remote Similarity	NPC224970
0.6667	Remote Similarity	NPC214428
0.6667	Remote Similarity	NPC312645
0.6652	Remote Similarity	NPC478158
0.665	Remote Similarity	NPC222029
0.665	Remote Similarity	NPC61013
0.6649	Remote Similarity	NPC207554
0.6638	Remote Similarity	NPC64216
0.6638	Remote Similarity	NPC77777
0.6636	Remote Similarity	NPC473298
0.6633	Remote Similarity	NPC242000
0.6627	Remote Similarity	NPC478006
0.6623	Remote Similarity	NPC123839
0.6622	Remote Similarity	NPC473376
0.662	Remote Similarity	NPC197335
0.662	Remote Similarity	NPC181928
0.6619	Remote Similarity	NPC248862
0.6618	Remote Similarity	NPC471122
0.6617	Remote Similarity	NPC117032
0.6609	Remote Similarity	NPC219397
0.6608	Remote Similarity	NPC71238
0.6606	Remote Similarity	NPC203628
0.6604	Remote Similarity	NPC99043
0.6604	Remote Similarity	NPC218594
0.6602	Remote Similarity	NPC315467
0.66	Remote Similarity	NPC473329
0.659	Remote Similarity	NPC18890
0.6585	Remote Similarity	NPC472102
0.6585	Remote Similarity	NPC309531
0.6584	Remote Similarity	NPC469903
0.6584	Remote Similarity	NPC151171
0.6574	Remote Similarity	NPC150308
0.6574	Remote Similarity	NPC303374
0.657	Remote Similarity	NPC471124
0.6565	Remote Similarity	NPC118940
0.6562	Remote Similarity	NPC232600
0.6561	Remote Similarity	NPC245916
0.656	Remote Similarity	NPC5630
0.6553	Remote Similarity	NPC286871
0.6549	Remote Similarity	NPC87714
0.6544	Remote Similarity	NPC94862
0.6537	Remote Similarity	NPC469901
0.6537	Remote Similarity	NPC469902
0.6537	Remote Similarity	NPC89508
0.6535	Remote Similarity	NPC266249
0.6528	Remote Similarity	NPC49184
0.6528	Remote Similarity	NPC52262
0.6528	Remote Similarity	NPC300299
0.6528	Remote Similarity	NPC173295
0.6522	Remote Similarity	NPC54981
0.6516	Remote Similarity	NPC34717
0.6515	Remote Similarity	NPC139373
0.6513	Remote Similarity	NPC24370
0.6513	Remote Similarity	NPC319232
0.6509	Remote Similarity	NPC314817
0.6509	Remote Similarity	NPC66191
0.6509	Remote Similarity	NPC316297
0.6504	Remote Similarity	NPC243782
0.6502	Remote Similarity	NPC154922
0.65	Remote Similarity	NPC223242
0.6498	Remote Similarity	NPC314056
0.6496	Remote Similarity	NPC303658
0.6493	Remote Similarity	NPC242269
0.6488	Remote Similarity	NPC113946
0.6488	Remote Similarity	NPC284888
0.6486	Remote Similarity	NPC303214
0.6486	Remote Similarity	NPC472293
0.6485	Remote Similarity	NPC314223
0.6484	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 NPC471198 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	571
0.2-0.3	890
0.3-0.4	1701
0.4-0.5	2525
0.5-0.6	2061
0.6-0.7	1082
0.7-0.8	89
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
0.7745	Intermediate Similarity	NPD5042	Phase 1
0.7673	Intermediate Similarity	NPD6557	Phase 2
0.7427	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5856	Discontinued
0.7241	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD8240	Discontinued
0.7039	Intermediate Similarity	NPD7688	Phase 1
0.7031	Intermediate Similarity	NPD8311	Discontinued
0.6971	Remote Similarity	NPD3989	Phase 3
0.6963	Remote Similarity	NPD7569	Approved
0.6963	Remote Similarity	NPD7570	Approved
0.694	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD3990	Phase 3
0.6934	Remote Similarity	NPD4515	Suspended
0.6923	Remote Similarity	NPD6199	Discontinued
0.6912	Remote Similarity	NPD5515	Phase 2
0.6893	Remote Similarity	NPD5997	Discontinued
0.6866	Remote Similarity	NPD3964	Approved
0.6852	Remote Similarity	NPD1059	Phase 2
0.6847	Remote Similarity	NPD3947	Discontinued
0.6833	Remote Similarity	NPD6532	Discontinued
0.683	Remote Similarity	NPD2509	Approved
0.683	Remote Similarity	NPD2510	Approved
0.6827	Remote Similarity	NPD4091	Approved
0.6818	Remote Similarity	NPD6805	Discontinued
0.6814	Remote Similarity	NPD7470	Discontinued
0.681	Remote Similarity	NPD6878	Phase 2
0.681	Remote Similarity	NPD6879	Phase 2
0.6802	Remote Similarity	NPD3802	Phase 3
0.6794	Remote Similarity	NPD3992	Approved
0.6794	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3994	Approved
0.6794	Remote Similarity	NPD4092	Approved
0.6794	Remote Similarity	NPD3991	Approved
0.6794	Remote Similarity	NPD3993	Approved
0.6794	Remote Similarity	NPD3995	Approved
0.6794	Remote Similarity	NPD3996	Approved
0.6793	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD6238	Discontinued
0.6787	Remote Similarity	NPD7817	Phase 1
0.6768	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3997	Approved
0.6762	Remote Similarity	NPD3998	Approved
0.6762	Remote Similarity	NPD3999	Approved
0.6756	Remote Similarity	NPD7232	Discontinued
0.6753	Remote Similarity	NPD6770	Approved
0.6751	Remote Similarity	NPD1802	Approved
0.6751	Remote Similarity	NPD1801	Approved
0.6732	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD5942	Approved
0.6717	Remote Similarity	NPD5941	Approved
0.6714	Remote Similarity	NPD5923	Phase 1
0.6711	Remote Similarity	NPD7225	Discontinued
0.6699	Remote Similarity	NPD3522	Approved
0.6699	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD3393	Approved
0.6696	Remote Similarity	NPD4982	Discontinued
0.6696	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD3394	Approved
0.6696	Remote Similarity	NPD3389	Approved
0.6695	Remote Similarity	NPD4301	Approved
0.6683	Remote Similarity	NPD7105	Phase 1
0.6681	Remote Similarity	NPD4356	Discontinued
0.6681	Remote Similarity	NPD6486	Approved
0.6681	Remote Similarity	NPD3441	Approved
0.6681	Remote Similarity	NPD6487	Approved
0.6681	Remote Similarity	NPD3442	Approved
0.6667	Remote Similarity	NPD6218	Discontinued
0.6667	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6176	Phase 1
0.664	Remote Similarity	NPD7397	Approved
0.664	Remote Similarity	NPD7398	Approved
0.6639	Remote Similarity	NPD7853	Phase 2
0.6638	Remote Similarity	NPD1623	Approved
0.6638	Remote Similarity	NPD6752	Phase 1
0.6638	Remote Similarity	NPD6753	Phase 1
0.6638	Remote Similarity	NPD7605	Discovery
0.6637	Remote Similarity	NPD3371	Approved
0.6618	Remote Similarity	NPD7599	Phase 2
0.6617	Remote Similarity	NPD3248	Phase 1
0.6612	Remote Similarity	NPD4946	Phase 2
0.6606	Remote Similarity	NPD5077	Approved
0.6606	Remote Similarity	NPD5076	Approved
0.6603	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6995	Phase 1
0.6595	Remote Similarity	NPD2813	Phase 3
0.6595	Remote Similarity	NPD1591	Approved
0.6595	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD3915	Approved
0.6592	Remote Similarity	NPD6519	Phase 2
0.659	Remote Similarity	NPD5851	Approved
0.659	Remote Similarity	NPD5852	Approved
0.6584	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD8289	Discontinued
0.6581	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7205	Discontinued
0.6573	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD3917	Approved
0.6565	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD3918	Approved
0.6565	Remote Similarity	NPD7573	Discontinued
0.655	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.654	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.654	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4082	Approved
0.6535	Remote Similarity	NPD4154	Approved
0.6532	Remote Similarity	NPD7572	Phase 2
0.6529	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6142	Phase 3
0.6529	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4493	Discontinued
0.6522	Remote Similarity	NPD5475	Discontinued
0.6514	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7600	Phase 2
0.6504	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4494	Approved
0.6494	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4492	Approved
0.6494	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7560	Approved
0.6489	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7994	Phase 2
0.6481	Remote Similarity	NPD6596	Phase 2
0.6481	Remote Similarity	NPD1960	Phase 2
0.6476	Remote Similarity	NPD5186	Approved
0.6476	Remote Similarity	NPD5183	Approved
0.6476	Remote Similarity	NPD8114	Approved
0.6476	Remote Similarity	NPD8115	Approved
0.6471	Remote Similarity	NPD7072	Phase 2
0.6468	Remote Similarity	NPD7528	Approved
0.6463	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5466	Approved
0.646	Remote Similarity	NPD3773	Approved
0.646	Remote Similarity	NPD3774	Approved
0.646	Remote Similarity	NPD3775	Approved
0.6457	Remote Similarity	NPD7776	Approved
0.6457	Remote Similarity	NPD3828	Approved
0.6456	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6659	Phase 2
0.6452	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7677	Discontinued
0.6447	Remote Similarity	NPD6260	Discontinued
0.6447	Remote Similarity	NPD4130	Phase 3
0.6441	Remote Similarity	NPD1996	Discontinued
0.6441	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.644	Remote Similarity	NPD4558	Phase 2
0.6439	Remote Similarity	NPD951	Approved
0.6439	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5293	Phase 2
0.6435	Remote Similarity	NPD4506	Discontinued
0.6435	Remote Similarity	NPD3874	Discontinued
0.6435	Remote Similarity	NPD3591	Approved
0.6435	Remote Similarity	NPD3592	Approved
0.6434	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD2893	Phase 3
0.6419	Remote Similarity	NPD5445	Approved
0.6419	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD7727	Phase 2
0.6416	Remote Similarity	NPD5552	Discontinued
0.6416	Remote Similarity	NPD6321	Discontinued
0.6415	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8160	Phase 2
0.641	Remote Similarity	NPD3353	Approved
0.6408	Remote Similarity	NPD8630	Approved
0.6406	Remote Similarity	NPD4412	Phase 2
0.6406	Remote Similarity	NPD5116	Phase 1
0.6402	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6249	Phase 2
0.64	Remote Similarity	NPD6248	Phase 2
0.6396	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6891	Phase 2
0.6388	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD8162	Phase 2
0.6387	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5003	Discontinued
0.6383	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD5024	Approved
0.6382	Remote Similarity	NPD4938	Phase 2
0.6376	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7010	Phase 3
0.6376	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7186	Phase 3
0.6375	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD1920	Approved
0.6373	Remote Similarity	NPD1919	Approved
0.6372	Remote Similarity	NPD7775	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