NPASS Compound

Structure

NPC280022 OpenBabel07101719152D 44 46 0 0 1 0 0 0 0 0999 V2000 2.5772 0.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2146 2.5907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2635 2.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9577 1.9216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7283 3.9290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5204 2.9508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6386 1.6637 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6519 1.5615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4440 0.5833 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6030 1.8705 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9088 2.2306 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4307 2.6418 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 1.6793 4.2380 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5897 1.3546 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 0 0 2 14 1 0 0 0 0 4 9 1 0 0 0 0 4 20 2 0 0 0 0 5 10 2 0 0 0 0 5 20 1 0 0 0 0 6 11 1 0 0 0 0 6 21 2 0 0 0 0 7 12 2 0 0 0 0 7 21 1 0 0 0 0 8 13 1 0 0 0 0 8 20 1 0 0 0 0 9 23 2 0 0 0 0 10 23 1 0 0 0 0 11 24 2 0 0 0 0 12 24 1 0 0 0 0 14 34 1 0 0 0 0 15 19 1 0 0 0 0 15 26 1 0 0 0 0 16 21 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 37 1 0 0 0 0 18 22 1 0 0 0 0 18 38 1 0 0 0 0 19 1 1 6 0 0 0 22 3 1 6 0 0 0 22 35 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 0 0 0 0 25 13 1 1 0 0 0 25 30 1 0 0 0 0 25 36 1 0 0 0 0 26 28 1 6 0 0 0 26 37 1 0 0 0 0 27 29 1 0 0 0 0 27 41 1 6 0 0 0 28 35 2 3 0 0 0 28 42 1 0 0 0 0 29 36 2 3 0 0 0 29 43 1 0 0 0 0 30 37 1 0 0 0 0 30 44 2 0 0 0 0 31 32 2 0 0 0 0 31 33 1 0 0 0 0 31 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.33
Volume:	620.21
LogP:	0.066
LogD:	0.332
LogS:	-2.48
# Rotatable Bonds:	18
TPSA:	223.83
# H-Bond Aceptor:	13
# H-Bond Donor:	10
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.076
Synthetic Accessibility Score:	4.153
Fsp3:	0.484
Lipinski Rule-of-5:	Rejected
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:	-6.313
MDCK Permeability:	3.27037378156092e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.977
Human Intestinal Absorption (HIA):	0.476
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	46.68239212036133%
Volume Distribution (VD):	0.641
Pgp-substrate:	49.504417419433594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.216
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	3.934
Half-life (T1/2):	0.57

ADMET: Toxicity

hERG Blockers:	0.257
Human Hepatotoxicity (H-HT):	0.93
Drug-inuced Liver Injury (DILI):	0.174
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.779
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.221
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC280022

Natural Product ID:	NPC280022
*Common Name:**	Spumigin A
IUPAC Name:	(2S,4S)-N-[(2S)-5-(diaminomethylideneamino)-1-hydroxypentan-2-yl]-1-[(2R)-2-[[(2R)-2-hydroxy-3-(4-hydroxyphenyl)propanoyl]amino]-4-(4-hydroxyphenyl)butanoyl]-4-methylpyrrolidine-2-carboxamide
Synonyms:	spumigin A
Standard InCHIKey:	LRHLULGPZSFCCN-VOTIHEBESA-N
Standard InCHI:	InChI=1S/C31H44N6O7/c1-19-15-26(28(42)35-22(18-38)3-2-14-34-31(32)33)37(17-19)30(44)25(13-8-20-4-9-23(39)10-5-20)36-29(43)27(41)16-21-6-11-24(40)12-7-21/h4-7,9-12,19,22,25-27,38-41H,2-3,8,13-18H2,1H3,(H,35,42)(H,36,43)(H4,32,33,34)/t19-,22-,25+,26-,27+/m0/s1
SMILES:	OC[C@@H](N=C([C@@H]1C[C@@H](CN1C(=O)[C@H](N=C([C@@H](Cc1ccc(cc1)O)O)O)CCc1ccc(cc1)O)C)O)CCCNC(=N)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2147469
PubChem CID:	71458276
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:0000348] Peptides [CHEMONTID:0004830] Dipeptides

*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
NPO33248	anabaena compacta	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22950366]

☑ 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
EC50	5
Others	1

Activity Type	# Activity
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT214	Individual Protein	Cathepsin B	Homo sapiens	EC50	=	200.0	nM	PMID[527904]
NPT2534	Individual Protein	Thrombin	Bos taurus	EC50	=	2100.0	nM	PMID[527904]
NPT1720	Individual Protein	Plasminogen	Homo sapiens	EC50	=	4900.0	nM	PMID[527905]
NPT670	Individual Protein	Thrombin	Homo sapiens	EC50	=	7500.0	nM	PMID[527905]
NPT2	Others	Unspecified		EC50	=	26300.0	nM	PMID[527905]
NPT2	Others	Unspecified		Ratio EC50	=	10.0	n.a.	PMID[527904]

☑ 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 NPC280022 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	183
0.1-0.2	1015
0.2-0.3	4862
0.3-0.4	12377
0.4-0.5	16060
0.5-0.6	7024
0.6-0.7	830
0.7-0.8	233
0.8-0.85	85
0.85-0.9	20
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9437	High Similarity	NPC119652
0.9437	High Similarity	NPC97526
0.9157	High Similarity	NPC94862
0.8931	High Similarity	NPC63931
0.8846	High Similarity	NPC476268
0.8834	High Similarity	NPC475532
0.8817	High Similarity	NPC96275
0.878	High Similarity	NPC165285
0.878	High Similarity	NPC17698
0.8713	High Similarity	NPC51047
0.8712	High Similarity	NPC274198
0.8712	High Similarity	NPC276506
0.8712	High Similarity	NPC198254
0.865	High Similarity	NPC129486
0.8636	High Similarity	NPC16188
0.8563	High Similarity	NPC302715
0.8547	High Similarity	NPC246591
0.8545	High Similarity	NPC89831
0.8509	High Similarity	NPC475544
0.8509	High Similarity	NPC469243
0.8503	High Similarity	NPC196243
0.8497	Intermediate Similarity	NPC168861
0.8448	Intermediate Similarity	NPC470728
0.8391	Intermediate Similarity	NPC240130
0.8391	Intermediate Similarity	NPC61332
0.8375	Intermediate Similarity	NPC473580
0.8365	Intermediate Similarity	NPC202198
0.8354	Intermediate Similarity	NPC473491
0.8354	Intermediate Similarity	NPC223207
0.8353	Intermediate Similarity	NPC475409
0.8353	Intermediate Similarity	NPC475564
0.8353	Intermediate Similarity	NPC170302
0.8333	Intermediate Similarity	NPC102959
0.8333	Intermediate Similarity	NPC26108
0.8333	Intermediate Similarity	NPC471165
0.8312	Intermediate Similarity	NPC476989
0.8305	Intermediate Similarity	NPC477632
0.8305	Intermediate Similarity	NPC80514
0.8305	Intermediate Similarity	NPC477638
0.8304	Intermediate Similarity	NPC473404
0.8303	Intermediate Similarity	NPC304074
0.8303	Intermediate Similarity	NPC290755
0.8303	Intermediate Similarity	NPC471771
0.8286	Intermediate Similarity	NPC60516
0.8253	Intermediate Similarity	NPC328649
0.8246	Intermediate Similarity	NPC153554
0.8235	Intermediate Similarity	NPC473546
0.8232	Intermediate Similarity	NPC241794
0.8221	Intermediate Similarity	NPC244336
0.8187	Intermediate Similarity	NPC233702
0.8167	Intermediate Similarity	NPC477550
0.8167	Intermediate Similarity	NPC477552
0.8165	Intermediate Similarity	NPC311658
0.8144	Intermediate Similarity	NPC209463
0.8137	Intermediate Similarity	NPC262166
0.8129	Intermediate Similarity	NPC214988
0.8095	Intermediate Similarity	NPC66490
0.8077	Intermediate Similarity	NPC477551
0.8065	Intermediate Similarity	NPC313694
0.8065	Intermediate Similarity	NPC242159
0.8059	Intermediate Similarity	NPC137627
0.8059	Intermediate Similarity	NPC273755
0.8056	Intermediate Similarity	NPC329295
0.8037	Intermediate Similarity	NPC244509
0.8036	Intermediate Similarity	NPC302597
0.8025	Intermediate Similarity	NPC56685
0.8012	Intermediate Similarity	NPC136797
0.8	Intermediate Similarity	NPC328494
0.7989	Intermediate Similarity	NPC477631
0.7987	Intermediate Similarity	NPC267237
0.7978	Intermediate Similarity	NPC477636
0.7976	Intermediate Similarity	NPC61004
0.7965	Intermediate Similarity	NPC50016
0.7956	Intermediate Similarity	NPC477639
0.7953	Intermediate Similarity	NPC306804
0.7941	Intermediate Similarity	NPC475204
0.7941	Intermediate Similarity	NPC475123
0.7903	Intermediate Similarity	NPC81845
0.7898	Intermediate Similarity	NPC48202
0.788	Intermediate Similarity	NPC469443
0.7874	Intermediate Similarity	NPC45037
0.7849	Intermediate Similarity	NPC248670
0.7836	Intermediate Similarity	NPC46009
0.7831	Intermediate Similarity	NPC323336
0.7831	Intermediate Similarity	NPC326349
0.7824	Intermediate Similarity	NPC141957
0.7805	Intermediate Similarity	NPC261934
0.7805	Intermediate Similarity	NPC5194
0.7803	Intermediate Similarity	NPC473354
0.7778	Intermediate Similarity	NPC478005
0.7771	Intermediate Similarity	NPC269750
0.7771	Intermediate Similarity	NPC194671
0.7719	Intermediate Similarity	NPC294516
0.7719	Intermediate Similarity	NPC107938
0.7701	Intermediate Similarity	NPC159767
0.7701	Intermediate Similarity	NPC155506
0.7701	Intermediate Similarity	NPC279871
0.7697	Intermediate Similarity	NPC294951
0.7696	Intermediate Similarity	NPC295795
0.7679	Intermediate Similarity	NPC287757
0.7679	Intermediate Similarity	NPC319320
0.7661	Intermediate Similarity	NPC254700
0.7654	Intermediate Similarity	NPC81026
0.7632	Intermediate Similarity	NPC220060
0.763	Intermediate Similarity	NPC40234
0.7628	Intermediate Similarity	NPC326966
0.76	Intermediate Similarity	NPC476227
0.7598	Intermediate Similarity	NPC471050
0.7598	Intermediate Similarity	NPC471049
0.7598	Intermediate Similarity	NPC471048
0.7593	Intermediate Similarity	NPC266741
0.7592	Intermediate Similarity	NPC469444
0.7586	Intermediate Similarity	NPC230611
0.7584	Intermediate Similarity	NPC477637
0.7584	Intermediate Similarity	NPC476321
0.7574	Intermediate Similarity	NPC1390
0.7574	Intermediate Similarity	NPC62104
0.7542	Intermediate Similarity	NPC471526
0.7516	Intermediate Similarity	NPC257390
0.75	Intermediate Similarity	NPC473402
0.75	Intermediate Similarity	NPC325651
0.7486	Intermediate Similarity	NPC473305
0.7486	Intermediate Similarity	NPC163961
0.7485	Intermediate Similarity	NPC122590
0.7485	Intermediate Similarity	NPC315266
0.7474	Intermediate Similarity	NPC469445
0.747	Intermediate Similarity	NPC324081
0.7469	Intermediate Similarity	NPC251439
0.7459	Intermediate Similarity	NPC299806
0.7448	Intermediate Similarity	NPC219350
0.7448	Intermediate Similarity	NPC194699
0.744	Intermediate Similarity	NPC39431
0.7437	Intermediate Similarity	NPC478007
0.7429	Intermediate Similarity	NPC196091
0.7412	Intermediate Similarity	NPC324850
0.7401	Intermediate Similarity	NPC158277
0.7399	Intermediate Similarity	NPC22883
0.7399	Intermediate Similarity	NPC5719
0.7399	Intermediate Similarity	NPC217804
0.7399	Intermediate Similarity	NPC210377
0.7391	Intermediate Similarity	NPC132636
0.7384	Intermediate Similarity	NPC73655
0.7363	Intermediate Similarity	NPC478008
0.7363	Intermediate Similarity	NPC138083
0.7338	Intermediate Similarity	NPC6975
0.7333	Intermediate Similarity	NPC32064
0.7329	Intermediate Similarity	NPC6570
0.7326	Intermediate Similarity	NPC114806
0.7322	Intermediate Similarity	NPC276120
0.7317	Intermediate Similarity	NPC326241
0.7317	Intermediate Similarity	NPC52748
0.7314	Intermediate Similarity	NPC63040
0.7305	Intermediate Similarity	NPC2501
0.7299	Intermediate Similarity	NPC472923
0.7296	Intermediate Similarity	NPC277306
0.7296	Intermediate Similarity	NPC469442
0.7273	Intermediate Similarity	NPC252878
0.7268	Intermediate Similarity	NPC315542
0.7267	Intermediate Similarity	NPC24617
0.7258	Intermediate Similarity	NPC473378
0.7258	Intermediate Similarity	NPC473407
0.7257	Intermediate Similarity	NPC15068
0.7241	Intermediate Similarity	NPC133470
0.7241	Intermediate Similarity	NPC289776
0.7241	Intermediate Similarity	NPC191863
0.7233	Intermediate Similarity	NPC255447
0.7229	Intermediate Similarity	NPC314114
0.7229	Intermediate Similarity	NPC262077
0.7226	Intermediate Similarity	NPC46427
0.7225	Intermediate Similarity	NPC473450
0.7222	Intermediate Similarity	NPC127741
0.7222	Intermediate Similarity	NPC25539
0.7219	Intermediate Similarity	NPC300443
0.7211	Intermediate Similarity	NPC323662
0.7208	Intermediate Similarity	NPC202521
0.7208	Intermediate Similarity	NPC71684
0.7207	Intermediate Similarity	NPC164608
0.7204	Intermediate Similarity	NPC283207
0.7195	Intermediate Similarity	NPC150712
0.719	Intermediate Similarity	NPC283760
0.7188	Intermediate Similarity	NPC45191
0.7182	Intermediate Similarity	NPC475421
0.7181	Intermediate Similarity	NPC65714
0.7175	Intermediate Similarity	NPC186617
0.7169	Intermediate Similarity	NPC209509
0.716	Intermediate Similarity	NPC7817
0.716	Intermediate Similarity	NPC475168
0.7152	Intermediate Similarity	NPC91953
0.7143	Intermediate Similarity	NPC244866
0.7143	Intermediate Similarity	NPC200964
0.7143	Intermediate Similarity	NPC9373
0.7143	Intermediate Similarity	NPC476990
0.7135	Intermediate Similarity	NPC473693
0.7135	Intermediate Similarity	NPC471568
0.7134	Intermediate Similarity	NPC471201
0.7119	Intermediate Similarity	NPC473502
0.7111	Intermediate Similarity	NPC477462
0.7107	Intermediate Similarity	NPC469666
0.7107	Intermediate Similarity	NPC111428
0.7107	Intermediate Similarity	NPC473322

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 NPC280022 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	125
0.1-0.2	393
0.2-0.3	604
0.3-0.4	1658
0.4-0.5	3489
0.5-0.6	2348
0.6-0.7	495
0.7-0.8	33
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD8303	Discontinued
0.8447	Intermediate Similarity	NPD7495	Discontinued
0.8385	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD8019	Approved
0.8079	Intermediate Similarity	NPD7617	Discontinued
0.8025	Intermediate Similarity	NPD7523	Phase 3
0.8012	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5137	Approved
0.7771	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7450	Phase 2
0.7654	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7303	Discontinued
0.7578	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7485	Phase 3
0.7572	Intermediate Similarity	NPD7484	Phase 3
0.7531	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7131	Phase 3
0.7484	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3136	Phase 2
0.7425	Intermediate Similarity	NPD7613	Discontinued
0.7391	Intermediate Similarity	NPD6901	Phase 3
0.7378	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD8076	Discontinued
0.7232	Intermediate Similarity	NPD7608	Discontinued
0.7232	Intermediate Similarity	NPD4652	Approved
0.7226	Intermediate Similarity	NPD2562	Approved
0.7226	Intermediate Similarity	NPD2561	Approved
0.72	Intermediate Similarity	NPD2098	Approved
0.7152	Intermediate Similarity	NPD7978	Discontinued
0.7134	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6676	Phase 2
0.7117	Intermediate Similarity	NPD8172	Phase 2
0.7117	Intermediate Similarity	NPD5314	Approved
0.7117	Intermediate Similarity	NPD8173	Phase 2
0.7086	Intermediate Similarity	NPD2097	Approved
0.7073	Intermediate Similarity	NPD3555	Approved
0.7073	Intermediate Similarity	NPD3552	Approved
0.7073	Intermediate Similarity	NPD3553	Approved
0.7073	Intermediate Similarity	NPD3554	Approved
0.7059	Intermediate Similarity	NPD6419	Discontinued
0.7055	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7451	Discontinued
0.7019	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6073	Approved
0.7012	Intermediate Similarity	NPD2568	Approved
0.7006	Intermediate Similarity	NPD6681	Discovery
0.6995	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3062	Approved
0.6994	Remote Similarity	NPD3061	Approved
0.6994	Remote Similarity	NPD3059	Approved
0.6989	Remote Similarity	NPD5967	Approved
0.6975	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1330	Phase 2
0.6957	Remote Similarity	NPD5263	Approved
0.6951	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8031	Discontinued
0.6901	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3073	Approved
0.6899	Remote Similarity	NPD3071	Approved
0.6899	Remote Similarity	NPD3072	Approved
0.6898	Remote Similarity	NPD6557	Phase 2
0.6898	Remote Similarity	NPD6851	Approved
0.6898	Remote Similarity	NPD6853	Approved
0.6894	Remote Similarity	NPD4175	Approved
0.6894	Remote Similarity	NPD4177	Approved
0.6882	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3053	Approved
0.6875	Remote Similarity	NPD3055	Approved
0.6875	Remote Similarity	NPD7011	Discontinued
0.6871	Remote Similarity	NPD601	Approved
0.6871	Remote Similarity	NPD597	Approved
0.6871	Remote Similarity	NPD598	Approved
0.6865	Remote Similarity	NPD6297	Approved
0.6864	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3985	Discontinued
0.6855	Remote Similarity	NPD4659	Approved
0.6839	Remote Similarity	NPD16	Approved
0.6839	Remote Similarity	NPD317	Approved
0.6839	Remote Similarity	NPD856	Approved
0.6839	Remote Similarity	NPD318	Approved
0.6835	Remote Similarity	NPD4761	Approved
0.6835	Remote Similarity	NPD4762	Approved
0.6829	Remote Similarity	NPD1130	Approved
0.6829	Remote Similarity	NPD1136	Approved
0.6829	Remote Similarity	NPD1132	Approved
0.6813	Remote Similarity	NPD5310	Approved
0.6813	Remote Similarity	NPD5311	Approved
0.6807	Remote Similarity	NPD5725	Approved
0.6796	Remote Similarity	NPD2890	Approved
0.6796	Remote Similarity	NPD2888	Approved
0.6796	Remote Similarity	NPD2889	Approved
0.6796	Remote Similarity	NPD2017	Approved
0.6791	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3040	Approved
0.6788	Remote Similarity	NPD4153	Approved
0.6786	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2239	Approved
0.6786	Remote Similarity	NPD2240	Approved
0.6784	Remote Similarity	NPD8323	Discontinued
0.6766	Remote Similarity	NPD6852	Discontinued
0.6763	Remote Similarity	NPD3536	Discontinued
0.6763	Remote Similarity	NPD2874	Phase 2
0.6748	Remote Similarity	NPD4676	Approved
0.6738	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1423	Approved
0.6727	Remote Similarity	NPD6405	Approved
0.6727	Remote Similarity	NPD6407	Approved
0.6722	Remote Similarity	NPD5218	Approved
0.6722	Remote Similarity	NPD5219	Approved
0.672	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6863	Phase 2
0.6709	Remote Similarity	NPD7342	Discontinued
0.6707	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD817	Approved
0.6707	Remote Similarity	NPD3052	Approved
0.6707	Remote Similarity	NPD823	Approved
0.6707	Remote Similarity	NPD3054	Approved
0.6704	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4157	Discontinued
0.6688	Remote Similarity	NPD316	Approved
0.6687	Remote Similarity	NPD6346	Approved
0.6687	Remote Similarity	NPD3626	Phase 3
0.6687	Remote Similarity	NPD2584	Suspended
0.6667	Remote Similarity	NPD2458	Approved
0.6667	Remote Similarity	NPD4103	Phase 2
0.6667	Remote Similarity	NPD3638	Discontinued
0.6667	Remote Similarity	NPD9568	Approved
0.6667	Remote Similarity	NPD4621	Approved
0.6667	Remote Similarity	NPD2460	Phase 3
0.6667	Remote Similarity	NPD2459	Approved
0.6667	Remote Similarity	NPD3060	Approved
0.6667	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4619	Approved
0.6651	Remote Similarity	NPD8292	Phase 2
0.6651	Remote Similarity	NPD6796	Discontinued
0.665	Remote Similarity	NPD7810	Phase 3
0.665	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7811	Phase 3
0.6648	Remote Similarity	NPD2978	Approved
0.6648	Remote Similarity	NPD2977	Approved
0.6648	Remote Similarity	NPD5773	Approved
0.6648	Remote Similarity	NPD5772	Approved
0.6647	Remote Similarity	NPD555	Phase 2
0.6647	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3908	Approved
0.6646	Remote Similarity	NPD4677	Discontinued
0.6646	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8162	Phase 2
0.6632	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8070	Approved
0.6629	Remote Similarity	NPD6677	Suspended
0.6628	Remote Similarity	NPD3400	Discontinued
0.6627	Remote Similarity	NPD259	Phase 1
0.6627	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD9620	Approved
0.6626	Remote Similarity	NPD9619	Approved
0.6626	Remote Similarity	NPD9621	Approved
0.6625	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD9616	Approved
0.6624	Remote Similarity	NPD9615	Approved
0.6624	Remote Similarity	NPD9613	Approved
0.6615	Remote Similarity	NPD8025	Phase 2
0.6613	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3455	Phase 2
0.6609	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6088	Approved
0.6607	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD3125	Approved
0.6604	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6967	Phase 2
0.6596	Remote Similarity	NPD5445	Approved
0.6592	Remote Similarity	NPD4227	Discontinued
0.6588	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD9570	Approved
0.6587	Remote Similarity	NPD6623	Phase 3
0.6587	Remote Similarity	NPD5323	Approved
0.6587	Remote Similarity	NPD8416	Discontinued
0.6585	Remote Similarity	NPD9569	Approved
0.6582	Remote Similarity	NPD2218	Phase 2
0.6582	Remote Similarity	NPD5304	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