NPASS Compound

Structure

NPC475150 OpenBabel07101718182D 50 52 0 0 1 0 0 0 0 0999 V2000 -12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 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 3.4641 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -11.2583 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 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 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 8 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 32 1 0 0 0 0 12 33 1 0 0 0 0 13 36 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 33 1 0 0 0 0 17 34 1 0 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 19 40 1 0 0 0 0 20 40 1 0 0 0 0 21 41 1 0 0 0 0 22 26 1 0 0 0 0 22 29 2 0 0 0 0 23 32 1 0 0 0 0 23 34 1 0 0 0 0 24 37 1 0 0 0 0 24 38 1 0 0 0 0 25 35 1 0 0 0 0 25 42 1 0 0 0 0 27 37 1 0 0 0 0 28 36 1 0 0 0 0 29 31 1 0 0 0 0 30 35 1 0 0 0 0 30 39 1 0 0 0 0 31 43 1 0 0 0 0 32 44 2 0 0 0 0 33 49 1 0 0 0 0 34 48 1 0 0 0 0 35 45 1 0 0 0 0 36 50 1 0 0 0 0 37 48 1 0 0 0 0 38 42 2 3 0 0 0 38 46 1 0 0 0 0 39 41 2 3 0 0 0 39 47 1 0 0 0 0 40 49 1 0 0 0 0 40 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	706.51
Volume:	756.496
LogP:	3.517
LogD:	3.668
LogS:	-4.656
# Rotatable Bonds:	21
TPSA:	143.42
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.093
Synthetic Accessibility Score:	5.881
Fsp3:	0.875
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:	-4.841
MDCK Permeability:	7.073978486005217e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.133
20% Bioavailability (F20%):	0.637
30% Bioavailability (F30%):	0.66

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	95.12964630126953%
Volume Distribution (VD):	0.882
Pgp-substrate:	2.8225700855255127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.749

ADMET: Excretion

Clearance (CL):	13.316
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.734
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.369
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC475150

Natural Product ID:	NPC475150
*Common Name:**	Bistramide B
IUPAC Name:	3-hydroxy-N-[3-[8-[(E)-6-hydroxy-3,5-dimethylhept-4-enyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl]-2-methyl-4-[[2-[3-methyl-6-(2-oxopentyl)oxan-2-yl]acetyl]amino]butanamide
Synonyms:
Standard InCHIKey:	YNLOUHRJSXTTGL-QUPMIFSKSA-N
Standard InCHI:	InChI=1S/C40H70N2O8/c1-8-11-32(44)23-34-17-15-27(3)37(48-34)24-38(46)42-25-35(45)30(6)39(47)41-21-10-13-36-28(4)18-20-40(50-36)19-9-12-33(49-40)16-14-26(2)22-29(5)31(7)43/h22,26-28,30-31,33-37,43,45H,8-21,23-25H2,1-7H3,(H,41,47)(H,42,46)/b29-22+
SMILES:	CCCC(=O)CC1CCC(C(O1)CC(=O)NCC(C(C)C(=O)NCCCC2C(CCC3(O2)CCCC(O3)CCC(C)C=C(C)C(C)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499434
PubChem CID:	9987308
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:0001880] Gamma amino acids and derivatives

*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
NPO22842	Lissoclinum bistratum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608858]
NPO22842	Lissoclinum bistratum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7807120]
NPO22842	Lissoclinum bistratum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.1	ug.mL-1	PMID[522200]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.2	ug.mL-1	PMID[522200]
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.16	ug.mL-1	PMID[522200]
NPT319	Cell Line	B16	Mus musculus	IC50	=	1.2	ug.mL-1	PMID[522200]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.71	ug.mL-1	PMID[522200]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.32	ug.mL-1	PMID[522200]

☑ 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 NPC475150 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	92
0.1-0.2	563
0.2-0.3	2973
0.3-0.4	15692
0.4-0.5	13849
0.5-0.6	8317
0.6-0.7	1178
0.7-0.8	28
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9612	High Similarity	NPC469865
0.932	High Similarity	NPC473578
0.89	High Similarity	NPC475646
0.8614	High Similarity	NPC475503
0.7345	Intermediate Similarity	NPC201128
0.7317	Intermediate Similarity	NPC469494
0.7248	Intermediate Similarity	NPC180722
0.7248	Intermediate Similarity	NPC165332
0.7248	Intermediate Similarity	NPC195645
0.7213	Intermediate Similarity	NPC469515
0.7207	Intermediate Similarity	NPC271207
0.7207	Intermediate Similarity	NPC255175
0.7207	Intermediate Similarity	NPC206711
0.7207	Intermediate Similarity	NPC225978
0.7188	Intermediate Similarity	NPC314361
0.7143	Intermediate Similarity	NPC477793
0.7143	Intermediate Similarity	NPC329919
0.7111	Intermediate Similarity	NPC214821
0.7111	Intermediate Similarity	NPC298067
0.7105	Intermediate Similarity	NPC74035
0.7091	Intermediate Similarity	NPC189629
0.7087	Intermediate Similarity	NPC69469
0.7077	Intermediate Similarity	NPC75318
0.7064	Intermediate Similarity	NPC5418
0.7045	Intermediate Similarity	NPC243680
0.7045	Intermediate Similarity	NPC200788
0.7043	Intermediate Similarity	NPC475918
0.7037	Intermediate Similarity	NPC472199
0.7034	Intermediate Similarity	NPC29501
0.7025	Intermediate Similarity	NPC316325
0.7023	Intermediate Similarity	NPC145899
0.7009	Intermediate Similarity	NPC315836
0.7009	Intermediate Similarity	NPC313668
0.7007	Intermediate Similarity	NPC61717
0.7007	Intermediate Similarity	NPC244380
0.7	Intermediate Similarity	NPC76999
0.6992	Remote Similarity	NPC180770
0.6972	Remote Similarity	NPC478036
0.6972	Remote Similarity	NPC478037
0.6947	Remote Similarity	NPC235772
0.6947	Remote Similarity	NPC280941
0.694	Remote Similarity	NPC82931
0.694	Remote Similarity	NPC210729
0.694	Remote Similarity	NPC172365
0.693	Remote Similarity	NPC477198
0.6923	Remote Similarity	NPC119794
0.6923	Remote Similarity	NPC73829
0.6911	Remote Similarity	NPC313802
0.6911	Remote Similarity	NPC477515
0.6911	Remote Similarity	NPC314268
0.6911	Remote Similarity	NPC67917
0.6909	Remote Similarity	NPC3568
0.6909	Remote Similarity	NPC17290
0.6909	Remote Similarity	NPC192066
0.6909	Remote Similarity	NPC256570
0.6909	Remote Similarity	NPC472198
0.6906	Remote Similarity	NPC36463
0.6906	Remote Similarity	NPC298005
0.6905	Remote Similarity	NPC313333
0.6905	Remote Similarity	NPC313342
0.6905	Remote Similarity	NPC314512
0.6905	Remote Similarity	NPC314451
0.6897	Remote Similarity	NPC476740
0.6897	Remote Similarity	NPC476738
0.6889	Remote Similarity	NPC162910
0.6885	Remote Similarity	NPC6531
0.6881	Remote Similarity	NPC472197
0.6881	Remote Similarity	NPC314500
0.687	Remote Similarity	NPC473816
0.687	Remote Similarity	NPC475367
0.687	Remote Similarity	NPC309398
0.687	Remote Similarity	NPC78189
0.687	Remote Similarity	NPC474581
0.6866	Remote Similarity	NPC302276
0.6866	Remote Similarity	NPC265908
0.6864	Remote Similarity	NPC24389
0.686	Remote Similarity	NPC471645
0.6846	Remote Similarity	NPC139585
0.6846	Remote Similarity	NPC475472
0.6842	Remote Similarity	NPC175531
0.6842	Remote Similarity	NPC316250
0.6838	Remote Similarity	NPC475394
0.6838	Remote Similarity	NPC251330
0.6838	Remote Similarity	NPC475152
0.6838	Remote Similarity	NPC475584
0.6825	Remote Similarity	NPC314629
0.6822	Remote Similarity	NPC477959
0.6822	Remote Similarity	NPC316205
0.6822	Remote Similarity	NPC86005
0.6822	Remote Similarity	NPC315387
0.6814	Remote Similarity	NPC234542
0.681	Remote Similarity	NPC14537
0.6803	Remote Similarity	NPC30196
0.6789	Remote Similarity	NPC242503
0.6789	Remote Similarity	NPC43074
0.6789	Remote Similarity	NPC209047
0.6789	Remote Similarity	NPC74672
0.6789	Remote Similarity	NPC139782
0.6788	Remote Similarity	NPC298469
0.6788	Remote Similarity	NPC69176
0.6788	Remote Similarity	NPC284625
0.6788	Remote Similarity	NPC141669
0.6788	Remote Similarity	NPC475892
0.6788	Remote Similarity	NPC193579
0.6786	Remote Similarity	NPC183449
0.6786	Remote Similarity	NPC197294
0.6786	Remote Similarity	NPC8098
0.6783	Remote Similarity	NPC313569
0.6761	Remote Similarity	NPC475527
0.6757	Remote Similarity	NPC70323
0.6757	Remote Similarity	NPC35269
0.6757	Remote Similarity	NPC23454
0.6757	Remote Similarity	NPC262312
0.6754	Remote Similarity	NPC473224
0.6752	Remote Similarity	NPC271269
0.6752	Remote Similarity	NPC473252
0.6727	Remote Similarity	NPC15851
0.6727	Remote Similarity	NPC263545
0.6727	Remote Similarity	NPC111567
0.6727	Remote Similarity	NPC309898
0.6727	Remote Similarity	NPC473950
0.6727	Remote Similarity	NPC186840
0.6727	Remote Similarity	NPC473581
0.6727	Remote Similarity	NPC473604
0.6727	Remote Similarity	NPC475125
0.6726	Remote Similarity	NPC167380
0.6724	Remote Similarity	NPC474563
0.6723	Remote Similarity	NPC474725
0.6713	Remote Similarity	NPC100612
0.6713	Remote Similarity	NPC174336
0.6713	Remote Similarity	NPC113620
0.6713	Remote Similarity	NPC187497
0.6713	Remote Similarity	NPC475599
0.6697	Remote Similarity	NPC159369
0.6697	Remote Similarity	NPC39290
0.6695	Remote Similarity	NPC475800
0.6694	Remote Similarity	NPC1111
0.6694	Remote Similarity	NPC261750
0.6694	Remote Similarity	NPC296361
0.6693	Remote Similarity	NPC315783
0.6667	Remote Similarity	NPC320089
0.6667	Remote Similarity	NPC470519
0.6667	Remote Similarity	NPC70733
0.6667	Remote Similarity	NPC56071
0.6667	Remote Similarity	NPC231271
0.6667	Remote Similarity	NPC314282
0.6667	Remote Similarity	NPC472616
0.6643	Remote Similarity	NPC265699
0.6642	Remote Similarity	NPC472430
0.6639	Remote Similarity	NPC307903
0.6639	Remote Similarity	NPC140251
0.6639	Remote Similarity	NPC193765
0.6637	Remote Similarity	NPC121857
0.6637	Remote Similarity	NPC45313
0.6636	Remote Similarity	NPC477865
0.6636	Remote Similarity	NPC477866
0.6636	Remote Similarity	NPC313670
0.6617	Remote Similarity	NPC120420
0.6614	Remote Similarity	NPC469943
0.6613	Remote Similarity	NPC201968
0.6613	Remote Similarity	NPC147707
0.6612	Remote Similarity	NPC297945
0.6612	Remote Similarity	NPC21713
0.6612	Remote Similarity	NPC126897
0.6612	Remote Similarity	NPC475608
0.661	Remote Similarity	NPC472615
0.661	Remote Similarity	NPC154601
0.6607	Remote Similarity	NPC282088
0.6607	Remote Similarity	NPC54961
0.6607	Remote Similarity	NPC156782
0.6607	Remote Similarity	NPC157353
0.6607	Remote Similarity	NPC158445
0.6604	Remote Similarity	NPC185949
0.6604	Remote Similarity	NPC107498
0.6593	Remote Similarity	NPC230889
0.6591	Remote Similarity	NPC316401
0.6585	Remote Similarity	NPC50694
0.6583	Remote Similarity	NPC329305
0.6581	Remote Similarity	NPC55336
0.6579	Remote Similarity	NPC278506
0.6577	Remote Similarity	NPC282705
0.6577	Remote Similarity	NPC475603
0.6577	Remote Similarity	NPC182632
0.6577	Remote Similarity	NPC61894
0.6571	Remote Similarity	NPC316249
0.6567	Remote Similarity	NPC472428
0.6567	Remote Similarity	NPC99864
0.6557	Remote Similarity	NPC60432
0.6555	Remote Similarity	NPC315531
0.6555	Remote Similarity	NPC315426
0.6535	Remote Similarity	NPC315915
0.6532	Remote Similarity	NPC315652
0.6532	Remote Similarity	NPC7905
0.6529	Remote Similarity	NPC127578
0.6529	Remote Similarity	NPC477997
0.6525	Remote Similarity	NPC469869
0.6522	Remote Similarity	NPC308567
0.6522	Remote Similarity	NPC261377
0.6522	Remote Similarity	NPC255592
0.6512	Remote Similarity	NPC204639

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 NPC475150 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	460
0.2-0.3	2711
0.3-0.4	4030
0.4-0.5	1448
0.5-0.6	342
0.6-0.7	66
0.7-0.8	5
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
0.7248	Intermediate Similarity	NPD7839	Suspended
0.7241	Intermediate Similarity	NPD6421	Discontinued
0.7165	Intermediate Similarity	NPD6914	Discontinued
0.7031	Intermediate Similarity	NPD8390	Approved
0.7031	Intermediate Similarity	NPD8391	Approved
0.7031	Intermediate Similarity	NPD8392	Approved
0.7025	Intermediate Similarity	NPD7500	Approved
0.6935	Remote Similarity	NPD8267	Approved
0.6935	Remote Similarity	NPD8268	Approved
0.6935	Remote Similarity	NPD8266	Approved
0.6935	Remote Similarity	NPD8269	Approved
0.6929	Remote Similarity	NPD8074	Phase 3
0.6905	Remote Similarity	NPD8342	Approved
0.6905	Remote Similarity	NPD8341	Approved
0.6905	Remote Similarity	NPD8299	Approved
0.6905	Remote Similarity	NPD8340	Approved
0.6789	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8451	Approved
0.6693	Remote Similarity	NPD7830	Approved
0.6693	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD8448	Approved
0.6667	Remote Similarity	NPD8444	Approved
0.6613	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7983	Approved
0.6567	Remote Similarity	NPD8415	Approved
0.6535	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4228	Discovery
0.6484	Remote Similarity	NPD8080	Discontinued
0.6462	Remote Similarity	NPD8273	Phase 1
0.6446	Remote Similarity	NPD8305	Approved
0.6446	Remote Similarity	NPD8306	Approved
0.6434	Remote Similarity	NPD7642	Approved
0.6429	Remote Similarity	NPD7641	Discontinued
0.6406	Remote Similarity	NPD8516	Approved
0.6406	Remote Similarity	NPD8513	Phase 3
0.6406	Remote Similarity	NPD8515	Approved
0.6406	Remote Similarity	NPD8517	Approved
0.6393	Remote Similarity	NPD6420	Discontinued
0.6379	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5778	Approved
0.6372	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD8336	Approved
0.6364	Remote Similarity	NPD8337	Approved
0.6357	Remote Similarity	NPD7623	Phase 3
0.6357	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD1719	Phase 1
0.6339	Remote Similarity	NPD46	Approved
0.6339	Remote Similarity	NPD6698	Approved
0.6311	Remote Similarity	NPD6413	Approved
0.6288	Remote Similarity	NPD7746	Phase 1
0.6288	Remote Similarity	NPD7747	Phase 1
0.6286	Remote Similarity	NPD8384	Approved
0.6286	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8307	Discontinued
0.6281	Remote Similarity	NPD8140	Approved
0.6279	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6686	Approved
0.6218	Remote Similarity	NPD8139	Approved
0.6218	Remote Similarity	NPD8085	Approved
0.6218	Remote Similarity	NPD8082	Approved
0.6218	Remote Similarity	NPD8086	Approved
0.6218	Remote Similarity	NPD8084	Approved
0.6218	Remote Similarity	NPD8138	Approved
0.6218	Remote Similarity	NPD8083	Approved
0.6198	Remote Similarity	NPD4211	Phase 1
0.6167	Remote Similarity	NPD8276	Approved
0.6167	Remote Similarity	NPD8275	Approved
0.6129	Remote Similarity	NPD8087	Discontinued
0.6116	Remote Similarity	NPD8081	Approved
0.6106	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6101	Approved
0.6066	Remote Similarity	NPD8393	Approved
0.6066	Remote Similarity	NPD5357	Phase 1
0.6066	Remote Similarity	NPD7333	Discontinued
0.6058	Remote Similarity	NPD8338	Approved
0.6032	Remote Similarity	NPD6430	Approved
0.6032	Remote Similarity	NPD6429	Approved
0.6016	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD7154	Phase 3
0.6	Remote Similarity	NPD6411	Approved
0.596	Remote Similarity	NPD8414	Discontinued
0.5954	Remote Similarity	NPD8347	Approved
0.5954	Remote Similarity	NPD8345	Approved
0.5954	Remote Similarity	NPD8346	Approved
0.594	Remote Similarity	NPD8328	Phase 3
0.5909	Remote Similarity	NPD4270	Approved
0.5909	Remote Similarity	NPD4269	Approved
0.5909	Remote Similarity	NPD7345	Approved
0.5906	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7637	Suspended
0.5841	Remote Similarity	NPD5786	Approved
0.5833	Remote Similarity	NPD3732	Approved
0.582	Remote Similarity	NPD7140	Approved
0.582	Remote Similarity	NPD7139	Approved
0.582	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6640	Phase 3
0.5794	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6941	Approved
0.5772	Remote Similarity	NPD2258	Approved
0.5772	Remote Similarity	NPD1407	Approved
0.5772	Remote Similarity	NPD2259	Approved
0.5763	Remote Similarity	NPD5282	Discontinued
0.5752	Remote Similarity	NPD5363	Approved
0.5746	Remote Similarity	NPD2838	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD8133	Approved
0.5734	Remote Similarity	NPD6333	Approved
0.5734	Remote Similarity	NPD6334	Approved
0.5727	Remote Similarity	NPD4252	Approved
0.5725	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5362	Discontinued
0.5714	Remote Similarity	NPD8174	Phase 2
0.5703	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD2257	Approved
0.5691	Remote Similarity	NPD8301	Approved
0.5691	Remote Similarity	NPD8300	Approved
0.5688	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5369	Approved
0.5672	Remote Similarity	NPD6921	Approved
0.5667	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8265	Approved
0.5656	Remote Similarity	NPD7639	Approved
0.5656	Remote Similarity	NPD6404	Discontinued
0.5656	Remote Similarity	NPD7640	Approved
0.5652	Remote Similarity	NPD4251	Approved
0.5652	Remote Similarity	NPD4250	Approved
0.5641	Remote Similarity	NPD5785	Approved
0.5641	Remote Similarity	NPD7838	Discovery
0.5635	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6436	Phase 3
0.5625	Remote Similarity	NPD6371	Approved
0.5625	Remote Similarity	NPD6435	Approved
0.562	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.5613	Remote Similarity	NPD8417	Discontinued
0.5612	Remote Similarity	NPD7319	Approved
0.5606	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD6935	Phase 3
0.5603	Remote Similarity	NPD2613	Approved
0.5603	Remote Similarity	NPD8449	Approved
0.5603	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8323	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