NPASS Compound

Structure

CID83790 OpenBabel06191715422D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.0000 -3.1756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8479 -1.2218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3479 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8479 -1.2218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8479 -2.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -2.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3479 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8479 -2.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3479 -2.0878 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 -1.6942 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7601 -1.2788 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 3.3479 -3.8198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 1.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 0.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -2.8968 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3 18 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 8 16 1 0 0 0 0 8 22 1 0 0 0 0 9 1 1 1 0 0 0 9 12 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 6 0 0 0 13 17 2 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 1 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 2 1 1 0 0 0 16 18 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.09
Volume:	331.823
LogP:	2.098
LogD:	1.665
LogS:	-2.065
# Rotatable Bonds:	3
TPSA:	73.13
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.871
Synthetic Accessibility Score:	4.567
Fsp3:	0.5
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:	-5.886
MDCK Permeability:	4.967402219335781e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.932
Plasma Protein Binding (PPB):	82.48342895507812%
Volume Distribution (VD):	1.204
Pgp-substrate:	32.6511344909668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.434
CYP1A2-substrate:	0.525
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.41
CYP2C9-substrate:	0.745
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.239
CYP3A4-substrate:	0.845

ADMET: Excretion

Clearance (CL):	3.827
Half-life (T1/2):	0.783

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.585
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.069
Carcinogencity:	0.274
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.307

Download Data

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

Natural Product: NPC83790

Natural Product ID:	NPC83790
*Common Name:**	Watasemycins B
IUPAC Name:	n.a.
Synonyms:	Watasemycins B
Standard InCHIKey:	NOEXPDVJQLSPPC-ZXAISWHRSA-N
Standard InCHI:	InChI=1S/C16H20N2O3S2/c1-9-12(14-18(3)16(2,8-22-14)15(20)21)17-13(23-9)10-6-4-5-7-11(10)19/h4-7,9,12,14,19H,8H2,1-3H3,(H,20,21)/t9-,12+,14+,16+/m0/s1
SMILES:	C[C@@H]1SC(=N[C@H]1[C@H]1SC[C@](N1C)(C)C(=O)O)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651094
PubChem CID:	NA
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:0002404] Alpha amino acids [CHEMONTID:0004146] L-alpha-amino acids

*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
NPO30976	Streptomyces sp. cp32	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028889]

☑ 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
Ki	11

Activity Type	# Activity
Individual Protein	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Ki	=	4695.0	nM	PMID[468966]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Ki	=	3900.0	nM	PMID[468967]
NPT2776	Individual Protein	Serotonin 1e (5-HT1e) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[468967]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[468967]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[468967]
NPT425	Individual Protein	Serotonin 3a (5-HT3a) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[468967]
NPT1784	Individual Protein	Serotonin 5a (5-HT5a) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[468967]
NPT294	Individual Protein	Serotonin 6 (5-HT6) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[468967]
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[468967]
NPT973	Individual Protein	Serotonin 1b (5-HT1b) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[468967]
NPT974	Individual Protein	Serotonin 1d (5-HT1d) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[468967]

☑ 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 NPC83790 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	165
0.1-0.2	1828
0.2-0.3	10726
0.3-0.4	9006
0.4-0.5	17190
0.5-0.6	3369
0.6-0.7	388
0.7-0.8	21
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC128237
0.7971	Intermediate Similarity	NPC86966
0.7971	Intermediate Similarity	NPC324702
0.7899	Intermediate Similarity	NPC112823
0.7399	Intermediate Similarity	NPC329731
0.7394	Intermediate Similarity	NPC315388
0.7299	Intermediate Similarity	NPC4910
0.7246	Intermediate Similarity	NPC227553
0.7222	Intermediate Similarity	NPC326349
0.7222	Intermediate Similarity	NPC323336
0.7161	Intermediate Similarity	NPC468984
0.7151	Intermediate Similarity	NPC184933
0.7151	Intermediate Similarity	NPC59827
0.7097	Intermediate Similarity	NPC476989
0.7078	Intermediate Similarity	NPC242159
0.7078	Intermediate Similarity	NPC313694
0.707	Intermediate Similarity	NPC266741
0.7033	Intermediate Similarity	NPC477527
0.7025	Intermediate Similarity	NPC81026
0.7	Intermediate Similarity	NPC163674
0.6983	Remote Similarity	NPC477526
0.6981	Remote Similarity	NPC16188
0.6975	Remote Similarity	NPC261934
0.6975	Remote Similarity	NPC5194
0.6975	Remote Similarity	NPC262166
0.6939	Remote Similarity	NPC474862
0.6914	Remote Similarity	NPC233702
0.6894	Remote Similarity	NPC13470
0.6871	Remote Similarity	NPC202198
0.6871	Remote Similarity	NPC56685
0.6859	Remote Similarity	NPC89489
0.6857	Remote Similarity	NPC153554
0.6855	Remote Similarity	NPC471680
0.6852	Remote Similarity	NPC473491
0.6849	Remote Similarity	NPC319950
0.6842	Remote Similarity	NPC478147
0.6821	Remote Similarity	NPC476353
0.6805	Remote Similarity	NPC63931
0.68	Remote Similarity	NPC171372
0.6788	Remote Similarity	NPC473580
0.6781	Remote Similarity	NPC5932
0.6776	Remote Similarity	NPC296712
0.6757	Remote Similarity	NPC56634
0.6753	Remote Similarity	NPC326966
0.6732	Remote Similarity	NPC325651
0.6732	Remote Similarity	NPC300315
0.6727	Remote Similarity	NPC39431
0.6724	Remote Similarity	NPC318930
0.6724	Remote Similarity	NPC317362
0.6711	Remote Similarity	NPC27581
0.6711	Remote Similarity	NPC142577
0.671	Remote Similarity	NPC244866
0.6706	Remote Similarity	NPC472923
0.669	Remote Similarity	NPC317254
0.6687	Remote Similarity	NPC244509
0.6687	Remote Similarity	NPC476268
0.6667	Remote Similarity	NPC61004
0.6667	Remote Similarity	NPC145178
0.6667	Remote Similarity	NPC475350
0.6667	Remote Similarity	NPC14877
0.6647	Remote Similarity	NPC475123
0.6647	Remote Similarity	NPC475204
0.6645	Remote Similarity	NPC257390
0.6645	Remote Similarity	NPC45191
0.6644	Remote Similarity	NPC473050
0.6644	Remote Similarity	NPC473051
0.6629	Remote Similarity	NPC317725
0.6629	Remote Similarity	NPC477637
0.6629	Remote Similarity	NPC326407
0.6627	Remote Similarity	NPC475544
0.6627	Remote Similarity	NPC469243
0.6621	Remote Similarity	NPC118202
0.6605	Remote Similarity	NPC473804
0.6603	Remote Similarity	NPC328070
0.6593	Remote Similarity	NPC3371
0.6588	Remote Similarity	NPC241794
0.6587	Remote Similarity	NPC256689
0.6587	Remote Similarity	NPC123011
0.6585	Remote Similarity	NPC476444
0.6585	Remote Similarity	NPC283783
0.6582	Remote Similarity	NPC6570
0.6571	Remote Similarity	NPC137627
0.6568	Remote Similarity	NPC244336
0.6564	Remote Similarity	NPC311658
0.6564	Remote Similarity	NPC119569
0.6564	Remote Similarity	NPC251036
0.6543	Remote Similarity	NPC322878
0.6543	Remote Similarity	NPC106183
0.6541	Remote Similarity	NPC473052
0.6541	Remote Similarity	NPC473055
0.6536	Remote Similarity	NPC476249
0.6534	Remote Similarity	NPC26108
0.6532	Remote Similarity	NPC141957
0.6532	Remote Similarity	NPC302597
0.6531	Remote Similarity	NPC82963
0.6525	Remote Similarity	NPC231705
0.6524	Remote Similarity	NPC189908
0.6514	Remote Similarity	NPC89831
0.6512	Remote Similarity	NPC223207
0.651	Remote Similarity	NPC283760
0.6505	Remote Similarity	NPC477638
0.6505	Remote Similarity	NPC477632
0.6503	Remote Similarity	NPC258056
0.65	Remote Similarity	NPC48202
0.65	Remote Similarity	NPC322526
0.6494	Remote Similarity	NPC129486
0.6486	Remote Similarity	NPC38458
0.6486	Remote Similarity	NPC311737
0.6479	Remote Similarity	NPC142297
0.6478	Remote Similarity	NPC109580
0.6475	Remote Similarity	NPC318154
0.6474	Remote Similarity	NPC290755
0.6474	Remote Similarity	NPC471771
0.6474	Remote Similarity	NPC304074
0.6467	Remote Similarity	NPC477636
0.646	Remote Similarity	NPC197921
0.6458	Remote Similarity	NPC474149
0.6452	Remote Similarity	NPC477839
0.6441	Remote Similarity	NPC165285
0.6441	Remote Similarity	NPC471165
0.6437	Remote Similarity	NPC294516
0.6437	Remote Similarity	NPC107938
0.6434	Remote Similarity	NPC153690
0.642	Remote Similarity	NPC91953
0.642	Remote Similarity	NPC469360
0.6419	Remote Similarity	NPC106551
0.6419	Remote Similarity	NPC281686
0.6419	Remote Similarity	NPC188867
0.6398	Remote Similarity	NPC477631
0.6398	Remote Similarity	NPC471201
0.6384	Remote Similarity	NPC475532
0.638	Remote Similarity	NPC314388
0.638	Remote Similarity	NPC315283
0.6375	Remote Similarity	NPC6913
0.6364	Remote Similarity	NPC274198
0.6364	Remote Similarity	NPC46009
0.6364	Remote Similarity	NPC40234
0.6364	Remote Similarity	NPC470824
0.6364	Remote Similarity	NPC276506
0.6364	Remote Similarity	NPC198254
0.6358	Remote Similarity	NPC191863
0.6358	Remote Similarity	NPC133470
0.6358	Remote Similarity	NPC289776
0.6348	Remote Similarity	NPC279871
0.6347	Remote Similarity	NPC324081
0.6347	Remote Similarity	NPC20755
0.6343	Remote Similarity	NPC328649
0.6343	Remote Similarity	NPC209463
0.6341	Remote Similarity	NPC313867
0.6341	Remote Similarity	NPC316008
0.634	Remote Similarity	NPC246303
0.6328	Remote Similarity	NPC328494
0.6328	Remote Similarity	NPC230611
0.6325	Remote Similarity	NPC9373
0.6321	Remote Similarity	NPC75498
0.6319	Remote Similarity	NPC24101
0.6319	Remote Similarity	NPC96224
0.6312	Remote Similarity	NPC178902
0.6307	Remote Similarity	NPC280022
0.6303	Remote Similarity	NPC314358
0.6299	Remote Similarity	NPC307020
0.6298	Remote Similarity	NPC39822
0.6296	Remote Similarity	NPC477639
0.6292	Remote Similarity	NPC306804
0.6292	Remote Similarity	NPC273755
0.6292	Remote Similarity	NPC248670
0.6291	Remote Similarity	NPC239697
0.6289	Remote Similarity	NPC470392
0.6286	Remote Similarity	NPC155847
0.6286	Remote Similarity	NPC289381
0.6276	Remote Similarity	NPC478005
0.6259	Remote Similarity	NPC315921
0.6258	Remote Similarity	NPC4974
0.6257	Remote Similarity	NPC158277
0.6257	Remote Similarity	NPC473354
0.6257	Remote Similarity	NPC17698
0.6257	Remote Similarity	NPC159767
0.6257	Remote Similarity	NPC473402
0.6257	Remote Similarity	NPC136797
0.6257	Remote Similarity	NPC476227
0.6257	Remote Similarity	NPC155506
0.625	Remote Similarity	NPC105541
0.625	Remote Similarity	NPC163810
0.625	Remote Similarity	NPC243404
0.6243	Remote Similarity	NPC194671
0.6243	Remote Similarity	NPC269750
0.6243	Remote Similarity	NPC475421
0.6242	Remote Similarity	NPC202776
0.6242	Remote Similarity	NPC469666
0.6232	Remote Similarity	NPC246679
0.623	Remote Similarity	NPC167763
0.623	Remote Similarity	NPC470112
0.623	Remote Similarity	NPC470903
0.6228	Remote Similarity	NPC105717
0.6226	Remote Similarity	NPC246079
0.6222	Remote Similarity	NPC196243
0.6222	Remote Similarity	NPC50016
0.622	Remote Similarity	NPC251439
0.6216	Remote Similarity	NPC309808
0.6215	Remote Similarity	NPC186617

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 NPC83790 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	119
0.1-0.2	464
0.2-0.3	1083
0.3-0.4	1937
0.4-0.5	3806
0.5-0.6	1516
0.6-0.7	195
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD7133	Discontinued
0.7931	Intermediate Similarity	NPD468	Phase 1
0.7862	Intermediate Similarity	NPD2098	Approved
0.7778	Intermediate Similarity	NPD2517	Approved
0.7736	Intermediate Similarity	NPD2097	Approved
0.7716	Intermediate Similarity	NPD2516	Approved
0.7669	Intermediate Similarity	NPD4652	Approved
0.7483	Intermediate Similarity	NPD2044	Approved
0.7483	Intermediate Similarity	NPD2045	Approved
0.7483	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2051	Approved
0.7483	Intermediate Similarity	NPD21	Approved
0.7483	Intermediate Similarity	NPD2048	Approved
0.7483	Intermediate Similarity	NPD2047	Approved
0.7483	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2043	Approved
0.7483	Intermediate Similarity	NPD2046	Approved
0.7432	Intermediate Similarity	NPD5299	Approved
0.7394	Intermediate Similarity	NPD2888	Approved
0.7394	Intermediate Similarity	NPD2017	Approved
0.7394	Intermediate Similarity	NPD2889	Approved
0.7394	Intermediate Similarity	NPD2890	Approved
0.7368	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5323	Approved
0.7312	Intermediate Similarity	NPD3111	Phase 1
0.7301	Intermediate Similarity	NPD7494	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7303	Discontinued
0.7215	Intermediate Similarity	NPD3988	Approved
0.7215	Intermediate Similarity	NPD3987	Approved
0.7161	Intermediate Similarity	NPD2087	Approved
0.7161	Intermediate Similarity	NPD2088	Approved
0.7161	Intermediate Similarity	NPD2022	Approved
0.7159	Intermediate Similarity	NPD4435	Approved
0.7143	Intermediate Similarity	NPD3480	Approved
0.7117	Intermediate Similarity	NPD2513	Approved
0.7103	Intermediate Similarity	NPD3143	Discontinued
0.7102	Intermediate Similarity	NPD4434	Approved
0.7099	Intermediate Similarity	NPD2052	Approved
0.7093	Intermediate Similarity	NPD5485	Approved
0.7093	Intermediate Similarity	NPD5484	Approved
0.7073	Intermediate Similarity	NPD3007	Approved
0.7073	Intermediate Similarity	NPD2515	Approved
0.7055	Intermediate Similarity	NPD22	Approved
0.7055	Intermediate Similarity	NPD2053	Approved
0.7019	Intermediate Similarity	NPD6390	Discontinued
0.7014	Intermediate Similarity	NPD1759	Phase 1
0.7006	Intermediate Similarity	NPD2436	Approved
0.7006	Intermediate Similarity	NPD2437	Approved
0.6988	Remote Similarity	NPD7738	Approved
0.6988	Remote Similarity	NPD7737	Approved
0.698	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1330	Phase 2
0.6954	Remote Similarity	NPD4125	Approved
0.6944	Remote Similarity	NPD1758	Phase 1
0.6928	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5367	Discontinued
0.6897	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2013	Approved
0.6894	Remote Similarity	NPD5613	Approved
0.6894	Remote Similarity	NPD2014	Approved
0.6894	Remote Similarity	NPD2016	Approved
0.6894	Remote Similarity	NPD5614	Approved
0.6832	Remote Similarity	NPD6106	Discontinued
0.6831	Remote Similarity	NPD1105	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6255	Approved
0.6828	Remote Similarity	NPD6254	Approved
0.6828	Remote Similarity	NPD6256	Approved
0.681	Remote Similarity	NPD5230	Approved
0.681	Remote Similarity	NPD5229	Approved
0.6807	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3125	Approved
0.6797	Remote Similarity	NPD3136	Phase 2
0.6796	Remote Similarity	NPD6505	Approved
0.6796	Remote Similarity	NPD6504	Approved
0.679	Remote Similarity	NPD1787	Approved
0.679	Remote Similarity	NPD1786	Approved
0.679	Remote Similarity	NPD1785	Approved
0.6779	Remote Similarity	NPD6624	Discontinued
0.6774	Remote Similarity	NPD6253	Approved
0.6774	Remote Similarity	NPD6346	Approved
0.677	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4126	Approved
0.675	Remote Similarity	NPD4127	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1803	Phase 3
0.6727	Remote Similarity	NPD4646	Approved
0.6727	Remote Similarity	NPD4648	Approved
0.6727	Remote Similarity	NPD4647	Approved
0.6726	Remote Similarity	NPD4567	Approved
0.6726	Remote Similarity	NPD4566	Approved
0.6726	Remote Similarity	NPD4557	Approved
0.6711	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5745	Approved
0.671	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8303	Discontinued
0.6667	Remote Similarity	NPD3070	Discontinued
0.6647	Remote Similarity	NPD2891	Approved
0.6646	Remote Similarity	NPD3599	Approved
0.6629	Remote Similarity	NPD2852	Approved
0.6585	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1582	Approved
0.6585	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1581	Approved
0.6584	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5746	Approved
0.6566	Remote Similarity	NPD7131	Phase 3
0.6558	Remote Similarity	NPD4212	Discontinued
0.6554	Remote Similarity	NPD6093	Discontinued
0.6543	Remote Similarity	NPD5264	Approved
0.6543	Remote Similarity	NPD5265	Approved
0.6541	Remote Similarity	NPD3552	Approved
0.6541	Remote Similarity	NPD3555	Approved
0.6541	Remote Similarity	NPD3553	Approved
0.6541	Remote Similarity	NPD3554	Approved
0.6533	Remote Similarity	NPD3421	Phase 3
0.6531	Remote Similarity	NPD6189	Approved
0.6531	Remote Similarity	NPD3123	Discovery
0.6531	Remote Similarity	NPD6188	Approved
0.6529	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6332	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6303	Approved
0.6494	Remote Similarity	NPD6304	Approved
0.649	Remote Similarity	NPD4480	Approved
0.648	Remote Similarity	NPD6187	Approved
0.6449	Remote Similarity	NPD9712	Approved
0.6443	Remote Similarity	NPD3351	Approved
0.6443	Remote Similarity	NPD5303	Approved
0.6443	Remote Similarity	NPD5304	Approved
0.6443	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7978	Discontinued
0.6419	Remote Similarity	NPD5291	Approved
0.6419	Remote Similarity	NPD5292	Approved
0.6419	Remote Similarity	NPD9568	Approved
0.6413	Remote Similarity	NPD3335	Approved
0.64	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2543	Discontinued
0.6393	Remote Similarity	NPD3334	Approved
0.6392	Remote Similarity	NPD3350	Approved
0.6392	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD3151	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD2853	Approved
0.6377	Remote Similarity	NPD9710	Approved
0.6377	Remote Similarity	NPD9711	Approved
0.6364	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3692	Discontinued
0.6359	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD3674	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD255	Approved
0.6351	Remote Similarity	NPD256	Approved
0.6348	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD4739	Approved
0.6343	Remote Similarity	NPD2644	Approved
0.6343	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD1048	Approved
0.6325	Remote Similarity	NPD1979	Approved
0.6324	Remote Similarity	NPD2854	Approved
0.6324	Remote Similarity	NPD2855	Approved
0.6324	Remote Similarity	NPD2856	Approved
0.6316	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2183	Approved
0.631	Remote Similarity	NPD2184	Approved
0.6299	Remote Similarity	NPD4659	Approved
0.6296	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1444	Approved
0.6294	Remote Similarity	NPD1445	Approved
0.6279	Remote Similarity	NPD7495	Discontinued
0.6272	Remote Similarity	NPD7523	Phase 3
0.6259	Remote Similarity	NPD9273	Approved
0.6258	Remote Similarity	NPD7450	Phase 2
0.6258	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD5076	Approved
0.6257	Remote Similarity	NPD5077	Approved
0.6243	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5852	Approved
0.6237	Remote Similarity	NPD5851	Approved
0.6236	Remote Similarity	NPD4150	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD4273	Approved
0.6234	Remote Similarity	NPD2562	Approved
0.6234	Remote Similarity	NPD2561	Approved
0.6218	Remote Similarity	NPD1134	Approved
0.6218	Remote Similarity	NPD4103	Phase 2
0.6218	Remote Similarity	NPD1133	Approved
0.6218	Remote Similarity	NPD1129	Approved
0.6218	Remote Similarity	NPD1135	Approved
0.6218	Remote Similarity	NPD1131	Approved
0.6218	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2229	Approved
0.6216	Remote Similarity	NPD2228	Approved
0.6216	Remote Similarity	NPD2234	Approved
0.6205	Remote Similarity	NPD1978	Approved
0.6205	Remote Similarity	NPD3400	Discontinued
0.6205	Remote Similarity	NPD5481	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