NPASS Compound

Structure

NPC223207 OpenBabel07101719142D 62 65 0 0 1 0 0 0 0 0999 V2000 6.1935 1.6388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1910 -0.8097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5144 0.1888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6142 -0.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1384 0.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2491 2.2425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3334 1.8408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3591 3.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3117 5.0689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3658 5.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5276 2.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5534 3.8286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1008 4.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8658 -3.6405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5979 -3.6405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0066 3.6381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9808 2.2425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7319 -2.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8658 -4.6405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5979 -4.6405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8124 3.0459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7866 1.6502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8658 -1.6405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3658 5.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8318 4.0192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2851 3.8286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2461 0.1888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6773 0.7357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7319 -3.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6376 3.4269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0908 3.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7319 -5.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7023 2.0519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6477 3.6175 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8658 -0.6405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9161 3.6175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3951 4.8226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4090 0.7357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0790 1.6515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3691 4.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8932 2.6481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7317 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8795 -0.4759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3108 5.2243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6735 5.0131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4200 5.0689 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8522 -0.4759 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1616 2.6481 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5635 4.0192 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5893 5.4148 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.8106 1.6515 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 2.7319 -6.1405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5081 1.4597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0484 1.4060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1048 5.1319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8898 2.7307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3459 -0.7891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5548 -1.4218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1166 4.6320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4208 6.2182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8678 5.6053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 4 52 1 0 0 0 0 5 27 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 24 1 0 0 0 0 11 30 2 0 0 0 0 12 30 1 0 0 0 0 13 34 1 0 0 0 0 14 19 1 0 0 0 0 14 29 2 0 0 0 0 15 20 2 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 16 31 2 0 0 0 0 17 22 2 0 0 0 0 17 31 1 0 0 0 0 18 23 1 0 0 0 0 18 29 1 0 0 0 0 19 32 2 0 0 0 0 20 32 1 0 0 0 0 21 33 2 0 0 0 0 22 33 1 0 0 0 0 24 46 1 0 0 0 0 25 30 1 0 0 0 0 26 31 1 0 0 0 0 27 2 1 1 0 0 0 28 3 1 1 0 0 0 28 39 1 0 0 0 0 28 52 1 0 0 0 0 32 53 1 0 0 0 0 33 54 1 0 0 0 0 34 41 1 0 0 0 0 34 49 1 1 0 0 0 35 23 1 1 0 0 0 35 43 1 0 0 0 0 35 47 1 0 0 0 0 36 25 1 1 0 0 0 36 40 1 0 0 0 0 36 48 1 0 0 0 0 37 26 1 6 0 0 0 37 44 1 0 0 0 0 37 50 1 0 0 0 0 38 27 1 1 0 0 0 38 42 1 0 0 0 0 38 51 1 0 0 0 0 39 48 2 3 0 0 0 39 55 1 0 0 0 0 40 46 2 3 0 0 0 40 56 1 0 0 0 0 41 51 2 3 0 0 0 41 57 1 0 0 0 0 42 47 2 3 0 0 0 42 58 1 0 0 0 0 43 52 1 0 0 0 0 43 59 2 0 0 0 0 44 60 2 0 0 0 0 44 61 1 0 0 0 0 45 49 2 3 0 0 0 45 50 1 0 0 0 0 45 62 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	768.34
Volume:	800.512
LogP:	8.8
LogD:	4.092
LogS:	-7.081
# Rotatable Bonds:	6
TPSA:	153.23
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.097
Synthetic Accessibility Score:	4.909
Fsp3:	0.298
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.562
MDCK Permeability:	9.468458301853389e-06
Pgp-inhibitor:	0.929
Pgp-substrate:	0.863
Human Intestinal Absorption (HIA):	0.668
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	93.98583984375%
Volume Distribution (VD):	0.228
Pgp-substrate:	4.033390045166016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.453
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.267
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.686
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.671
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.631

ADMET: Excretion

Clearance (CL):	1.771
Half-life (T1/2):	0.023

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.881
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.097
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.841
Carcinogencity:	0.006
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.296

Download Data

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

Natural Product: NPC223207

Natural Product ID:	NPC223207
*Common Name:**	Oscillamide Y
IUPAC Name:	(2S)-2-[[(3S,6S,9S,12S,15R)-3-benzyl-12-[(2R)-butan-2-yl]-9-[2-(4-hydroxyphenyl)ethyl]-6,7-dimethyl-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentazacyclononadec-15-yl]carbamoylamino]-3-(4-hydroxyphenyl)propanoic acid
Synonyms:	Oscillamide Y
Standard InCHIKey:	KCAKUFQSCADGHZ-JNFDXLRCSA-N
Standard InCHI:	InChI=1S/C45H59N7O10/c1-5-27(2)38-42(58)47-35(23-18-29-14-19-32(53)20-15-29)43(59)52(4)28(3)39(55)48-36(25-30-11-7-6-8-12-30)40(56)46-24-10-9-13-34(41(57)51-38)49-45(62)50-37(44(60)61)26-31-16-21-33(54)22-17-31/h6-8,11-12,14-17,19-22,27-28,34-38,53-54H,5,9-10,13,18,23-26H2,1-4H3,(H,46,56)(H,47,58)(H,48,55)(H,51,57)(H,60,61)(H2,49,50,62)/t27-,28+,34-,35+,36+,37+,38+/m1/s1
SMILES:	CC[C@H]([C@@H]1N=C(O)[C@@H](CCCCN=C([C@@H](N=C([C@@H](N(C(=O)[C@@H](N=C1O)CCc1ccc(cc1)O)C)C)O)Cc1ccccc1)O)N=C(N[C@H](C(=O)O)Cc1ccc(cc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446236
PubChem CID:	15342746
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:0004831] Oligopeptides

*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
NPO33422	planktothrix spp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11520225]

☑ 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
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6400	Individual Protein	Carboxypeptidase B2 isoform A	Homo sapiens	IC50	=	400.0	nM	PMID[490406]
NPT2	Others	Unspecified		Inhibition	=	11.2	%	PMID[490404]
NPT2	Others	Unspecified		Inhibition	=	9.6	%	PMID[490404]

☑ 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 NPC223207 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	208
0.1-0.2	1194
0.2-0.3	7087
0.3-0.4	10342
0.4-0.5	15789
0.5-0.6	6921
0.6-0.7	801
0.7-0.8	289
0.8-0.85	43
0.85-0.9	11
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC471771
0.9933	High Similarity	NPC290755
0.9933	High Similarity	NPC304074
0.9799	High Similarity	NPC469243
0.9667	High Similarity	NPC475544
0.953	High Similarity	NPC473580
0.949	High Similarity	NPC196243
0.9359	High Similarity	NPC274198
0.9359	High Similarity	NPC198254
0.9236	High Similarity	NPC276506
0.8841	High Similarity	NPC153554
0.8824	High Similarity	NPC233702
0.8625	High Similarity	NPC63931
0.8591	High Similarity	NPC132636
0.8537	High Similarity	NPC475532
0.8519	High Similarity	NPC328649
0.8485	Intermediate Similarity	NPC165285
0.8442	Intermediate Similarity	NPC16188
0.843	Intermediate Similarity	NPC61332
0.843	Intermediate Similarity	NPC240130
0.8421	Intermediate Similarity	NPC94862
0.8354	Intermediate Similarity	NPC280022
0.8354	Intermediate Similarity	NPC129486
0.8333	Intermediate Similarity	NPC119652
0.8333	Intermediate Similarity	NPC97526
0.8313	Intermediate Similarity	NPC306804
0.8291	Intermediate Similarity	NPC202198
0.8286	Intermediate Similarity	NPC302715
0.8263	Intermediate Similarity	NPC17698
0.8263	Intermediate Similarity	NPC159767
0.8263	Intermediate Similarity	NPC155506
0.8255	Intermediate Similarity	NPC326966
0.8235	Intermediate Similarity	NPC473404
0.8232	Intermediate Similarity	NPC61004
0.82	Intermediate Similarity	NPC244866
0.8182	Intermediate Similarity	NPC141957
0.816	Intermediate Similarity	NPC241794
0.8144	Intermediate Similarity	NPC230611
0.8144	Intermediate Similarity	NPC89831
0.8121	Intermediate Similarity	NPC325651
0.8118	Intermediate Similarity	NPC45037
0.8118	Intermediate Similarity	NPC269750
0.8118	Intermediate Similarity	NPC194671
0.8117	Intermediate Similarity	NPC476989
0.8095	Intermediate Similarity	NPC273755
0.8095	Intermediate Similarity	NPC137627
0.8095	Intermediate Similarity	NPC248670
0.8084	Intermediate Similarity	NPC46009
0.8072	Intermediate Similarity	NPC107938
0.8072	Intermediate Similarity	NPC294516
0.8047	Intermediate Similarity	NPC158277
0.8047	Intermediate Similarity	NPC279871
0.8047	Intermediate Similarity	NPC473402
0.8037	Intermediate Similarity	NPC319320
0.8037	Intermediate Similarity	NPC287757
0.8013	Intermediate Similarity	NPC257390
0.8	Intermediate Similarity	NPC50016
0.7976	Intermediate Similarity	NPC40234
0.7964	Intermediate Similarity	NPC209463
0.7955	Intermediate Similarity	NPC102959
0.795	Intermediate Similarity	NPC56685
0.7941	Intermediate Similarity	NPC476227
0.7941	Intermediate Similarity	NPC26108
0.7937	Intermediate Similarity	NPC473491
0.7935	Intermediate Similarity	NPC48202
0.7931	Intermediate Similarity	NPC294951
0.7919	Intermediate Similarity	NPC477937
0.7911	Intermediate Similarity	NPC81026
0.791	Intermediate Similarity	NPC60516
0.7892	Intermediate Similarity	NPC289776
0.7892	Intermediate Similarity	NPC133470
0.7892	Intermediate Similarity	NPC191863
0.787	Intermediate Similarity	NPC475123
0.787	Intermediate Similarity	NPC475204
0.7848	Intermediate Similarity	NPC266741
0.784	Intermediate Similarity	NPC261934
0.784	Intermediate Similarity	NPC5194
0.784	Intermediate Similarity	NPC262166
0.7836	Intermediate Similarity	NPC473354
0.7836	Intermediate Similarity	NPC136797
0.7836	Intermediate Similarity	NPC471165
0.7833	Intermediate Similarity	NPC477638
0.7833	Intermediate Similarity	NPC477632
0.7818	Intermediate Similarity	NPC244336
0.7807	Intermediate Similarity	NPC478005
0.7802	Intermediate Similarity	NPC477552
0.7802	Intermediate Similarity	NPC477550
0.7771	Intermediate Similarity	NPC471526
0.7758	Intermediate Similarity	NPC323336
0.7758	Intermediate Similarity	NPC326349
0.7756	Intermediate Similarity	NPC242159
0.7756	Intermediate Similarity	NPC313694
0.775	Intermediate Similarity	NPC311658
0.7717	Intermediate Similarity	NPC477551
0.7716	Intermediate Similarity	NPC324081
0.7709	Intermediate Similarity	NPC163961
0.7709	Intermediate Similarity	NPC473305
0.7692	Intermediate Similarity	NPC477639
0.7684	Intermediate Similarity	NPC138083
0.7683	Intermediate Similarity	NPC39431
0.7677	Intermediate Similarity	NPC267237
0.7657	Intermediate Similarity	NPC32064
0.7654	Intermediate Similarity	NPC234069
0.7651	Intermediate Similarity	NPC27581
0.7647	Intermediate Similarity	NPC302597
0.7636	Intermediate Similarity	NPC476268
0.7636	Intermediate Similarity	NPC244509
0.763	Intermediate Similarity	NPC164608
0.7627	Intermediate Similarity	NPC471048
0.7627	Intermediate Similarity	NPC471050
0.7627	Intermediate Similarity	NPC471049
0.7614	Intermediate Similarity	NPC476321
0.7611	Intermediate Similarity	NPC477636
0.7611	Intermediate Similarity	NPC174122
0.7611	Intermediate Similarity	NPC64140
0.761	Intermediate Similarity	NPC168861
0.7602	Intermediate Similarity	NPC66490
0.7596	Intermediate Similarity	NPC329295
0.7584	Intermediate Similarity	NPC299806
0.7584	Intermediate Similarity	NPC71684
0.7582	Intermediate Similarity	NPC473322
0.7582	Intermediate Similarity	NPC111428
0.7557	Intermediate Similarity	NPC475409
0.7557	Intermediate Similarity	NPC170302
0.7557	Intermediate Similarity	NPC475564
0.7529	Intermediate Similarity	NPC472923
0.7527	Intermediate Similarity	NPC477631
0.7527	Intermediate Similarity	NPC469443
0.7514	Intermediate Similarity	NPC477637
0.75	Intermediate Similarity	NPC91953
0.7486	Intermediate Similarity	NPC328763
0.7484	Intermediate Similarity	NPC214988
0.7484	Intermediate Similarity	NPC255447
0.7473	Intermediate Similarity	NPC473407
0.7473	Intermediate Similarity	NPC473378
0.7468	Intermediate Similarity	NPC296712
0.7457	Intermediate Similarity	NPC196091
0.745	Intermediate Similarity	NPC283760
0.745	Intermediate Similarity	NPC319950
0.7444	Intermediate Similarity	NPC276120
0.7443	Intermediate Similarity	NPC473546
0.7442	Intermediate Similarity	NPC473502
0.744	Intermediate Similarity	NPC56635
0.7438	Intermediate Similarity	NPC197921
0.7433	Intermediate Similarity	NPC473450
0.7419	Intermediate Similarity	NPC478147
0.7403	Intermediate Similarity	NPC96275
0.7399	Intermediate Similarity	NPC186617
0.7391	Intermediate Similarity	NPC469360
0.7389	Intermediate Similarity	NPC315542
0.7383	Intermediate Similarity	NPC470546
0.7378	Intermediate Similarity	NPC9373
0.7374	Intermediate Similarity	NPC478007
0.7362	Intermediate Similarity	NPC314114
0.7358	Intermediate Similarity	NPC6570
0.7358	Intermediate Similarity	NPC127741
0.7356	Intermediate Similarity	NPC473693
0.7356	Intermediate Similarity	NPC471568
0.7326	Intermediate Similarity	NPC323662
0.7325	Intermediate Similarity	NPC45191
0.7322	Intermediate Similarity	NPC29531
0.7322	Intermediate Similarity	NPC51047
0.7315	Intermediate Similarity	NPC470545
0.7305	Intermediate Similarity	NPC473341
0.7303	Intermediate Similarity	NPC475421
0.73	Intermediate Similarity	NPC478008
0.7299	Intermediate Similarity	NPC315388
0.7292	Intermediate Similarity	NPC220060
0.7273	Intermediate Similarity	NPC101719
0.7273	Intermediate Similarity	NPC471592
0.7261	Intermediate Similarity	NPC120251
0.7254	Intermediate Similarity	NPC469444
0.7248	Intermediate Similarity	NPC106551
0.7248	Intermediate Similarity	NPC470544
0.7248	Intermediate Similarity	NPC188867
0.7248	Intermediate Similarity	NPC281686
0.7229	Intermediate Similarity	NPC254798
0.7225	Intermediate Similarity	NPC189116
0.7219	Intermediate Similarity	NPC469903
0.7216	Intermediate Similarity	NPC328494
0.7208	Intermediate Similarity	NPC222466
0.7204	Intermediate Similarity	NPC65714
0.7198	Intermediate Similarity	NPC235194
0.7193	Intermediate Similarity	NPC1390
0.7193	Intermediate Similarity	NPC62104
0.719	Intermediate Similarity	NPC474862
0.719	Intermediate Similarity	NPC142577
0.7189	Intermediate Similarity	NPC248822
0.7188	Intermediate Similarity	NPC314835
0.7188	Intermediate Similarity	NPC473360
0.7184	Intermediate Similarity	NPC254700
0.7182	Intermediate Similarity	NPC470903
0.7182	Intermediate Similarity	NPC470112
0.7182	Intermediate Similarity	NPC167763
0.7181	Intermediate Similarity	NPC317254
0.7178	Intermediate Similarity	NPC161069
0.7174	Intermediate Similarity	NPC246591
0.7166	Intermediate Similarity	NPC471563
0.7151	Intermediate Similarity	NPC114806
0.7143	Intermediate Similarity	NPC469445

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 NPC223207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	377
0.2-0.3	820
0.3-0.4	1429
0.4-0.5	3265
0.5-0.6	2512
0.6-0.7	561
0.7-0.8	50
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8608	High Similarity	NPD7495	Discontinued
0.8608	High Similarity	NPD8019	Approved
0.8571	High Similarity	NPD8303	Discontinued
0.8355	Intermediate Similarity	NPD7450	Phase 2
0.8176	Intermediate Similarity	NPD7523	Phase 3
0.7888	Intermediate Similarity	NPD7303	Discontinued
0.7866	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3136	Phase 2
0.7707	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7451	Discontinued
0.7611	Intermediate Similarity	NPD7617	Discontinued
0.761	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7608	Discontinued
0.7515	Intermediate Similarity	NPD7131	Phase 3
0.75	Intermediate Similarity	NPD8076	Discontinued
0.75	Intermediate Similarity	NPD7978	Discontinued
0.75	Intermediate Similarity	NPD7485	Phase 3
0.75	Intermediate Similarity	NPD7484	Phase 3
0.7486	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4652	Approved
0.7439	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD2098	Approved
0.7421	Intermediate Similarity	NPD6901	Phase 3
0.7394	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4677	Discontinued
0.731	Intermediate Similarity	NPD2097	Approved
0.7299	Intermediate Similarity	NPD2888	Approved
0.7299	Intermediate Similarity	NPD2889	Approved
0.7299	Intermediate Similarity	NPD2017	Approved
0.7299	Intermediate Similarity	NPD2890	Approved
0.729	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9568	Approved
0.7233	Intermediate Similarity	NPD6346	Approved
0.7219	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7720	Phase 2
0.7169	Intermediate Similarity	NPD7554	Discontinued
0.7167	Intermediate Similarity	NPD5445	Approved
0.7167	Intermediate Similarity	NPD6297	Approved
0.716	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6681	Discovery
0.7126	Intermediate Similarity	NPD8031	Discontinued
0.7125	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5137	Approved
0.711	Intermediate Similarity	NPD5967	Approved
0.7108	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5581	Approved
0.7104	Intermediate Similarity	NPD6853	Approved
0.7104	Intermediate Similarity	NPD6851	Approved
0.7095	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2562	Approved
0.7032	Intermediate Similarity	NPD2561	Approved
0.703	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6088	Approved
0.7006	Intermediate Similarity	NPD8323	Discontinued
0.7	Intermediate Similarity	NPD1330	Phase 2
0.7	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5263	Approved
0.6975	Remote Similarity	NPD3908	Approved
0.6964	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD255	Approved
0.6954	Remote Similarity	NPD256	Approved
0.6951	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1968	Approved
0.6946	Remote Similarity	NPD1967	Approved
0.6937	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3072	Approved
0.6923	Remote Similarity	NPD3073	Approved
0.6923	Remote Similarity	NPD3071	Approved
0.6914	Remote Similarity	NPD6623	Phase 3
0.6909	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8025	Phase 2
0.689	Remote Similarity	NPD3555	Approved
0.689	Remote Similarity	NPD6295	Approved
0.689	Remote Similarity	NPD3554	Approved
0.689	Remote Similarity	NPD6294	Approved
0.689	Remote Similarity	NPD3553	Approved
0.689	Remote Similarity	NPD3552	Approved
0.6871	Remote Similarity	NPD8643	Discontinued
0.6859	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4761	Approved
0.6859	Remote Similarity	NPD4762	Approved
0.6856	Remote Similarity	NPD6255	Approved
0.6856	Remote Similarity	NPD6254	Approved
0.6856	Remote Similarity	NPD6256	Approved
0.6852	Remote Similarity	NPD5745	Approved
0.6845	Remote Similarity	NPD3400	Discontinued
0.6842	Remote Similarity	NPD7613	Discontinued
0.6839	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7810	Phase 3
0.6839	Remote Similarity	NPD7811	Phase 3
0.6835	Remote Similarity	NPD3125	Approved
0.6829	Remote Similarity	NPD6073	Approved
0.6828	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD9569	Approved
0.6813	Remote Similarity	NPD3040	Approved
0.681	Remote Similarity	NPD5323	Approved
0.6809	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6253	Approved
0.68	Remote Similarity	NPD5355	Approved
0.68	Remote Similarity	NPD5356	Approved
0.6791	Remote Similarity	NPD6967	Phase 2
0.6788	Remote Similarity	NPD6852	Discontinued
0.6772	Remote Similarity	NPD4659	Approved
0.677	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4676	Approved
0.6765	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD259	Phase 1
0.6746	Remote Similarity	NPD8292	Phase 2
0.6739	Remote Similarity	NPD5484	Approved
0.6739	Remote Similarity	NPD5485	Approved
0.6733	Remote Similarity	NPD6189	Approved
0.6733	Remote Similarity	NPD6188	Approved
0.673	Remote Similarity	NPD5367	Discontinued
0.6728	Remote Similarity	NPD5746	Approved
0.6727	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5614	Approved
0.6725	Remote Similarity	NPD5613	Approved
0.671	Remote Similarity	NPD1759	Phase 1
0.6708	Remote Similarity	NPD4177	Approved
0.6708	Remote Similarity	NPD7828	Discontinued
0.6708	Remote Similarity	NPD4175	Approved
0.6707	Remote Similarity	NPD1519	Approved
0.6707	Remote Similarity	NPD1537	Approved
0.6707	Remote Similarity	NPD1538	Phase 1
0.6703	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3053	Approved
0.6687	Remote Similarity	NPD3055	Approved
0.6687	Remote Similarity	NPD5299	Approved
0.6687	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3536	Discontinued
0.6686	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6419	Discontinued
0.6685	Remote Similarity	NPD6747	Phase 1
0.6683	Remote Similarity	NPD6187	Approved
0.6667	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD555	Phase 2
0.6667	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8315	Phase 1
0.6667	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7283	Approved
0.6649	Remote Similarity	NPD6557	Phase 2
0.6648	Remote Similarity	NPD8070	Approved
0.6648	Remote Similarity	NPD6677	Suspended
0.6647	Remote Similarity	NPD6390	Discontinued
0.6647	Remote Similarity	NPD5481	Discontinued
0.6646	Remote Similarity	NPD4151	Approved
0.6645	Remote Similarity	NPD16	Approved
0.6645	Remote Similarity	NPD1758	Phase 1
0.6645	Remote Similarity	NPD318	Approved
0.6645	Remote Similarity	NPD856	Approved
0.6645	Remote Similarity	NPD317	Approved
0.6631	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3988	Approved
0.6628	Remote Similarity	NPD2013	Approved
0.6628	Remote Similarity	NPD2016	Approved
0.6628	Remote Similarity	NPD2014	Approved
0.6628	Remote Similarity	NPD3987	Approved
0.6627	Remote Similarity	NPD8172	Phase 2
0.6627	Remote Similarity	NPD8173	Phase 2
0.6627	Remote Similarity	NPD2568	Approved
0.6627	Remote Similarity	NPD5725	Approved
0.6626	Remote Similarity	NPD9536	Phase 1
0.6626	Remote Similarity	NPD9537	Phase 1
0.6625	Remote Similarity	NPD5311	Approved
0.6625	Remote Similarity	NPD196	Phase 1
0.6625	Remote Similarity	NPD5310	Approved
0.6624	Remote Similarity	NPD7342	Discontinued
0.6611	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2239	Approved
0.6607	Remote Similarity	NPD2240	Approved
0.6607	Remote Similarity	NPD1522	Approved
0.6607	Remote Similarity	NPD4173	Approved
0.6607	Remote Similarity	NPD4172	Approved
0.6607	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1523	Approved
0.6606	Remote Similarity	NPD4153	Approved
0.6606	Remote Similarity	NPD8416	Discontinued
0.6604	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD4565	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data