NPASS Compound

Structure

NPC475503 OpenBabel07101719192D 50 51 0 0 1 0 0 0 0 0999 V2000 -17.3205 -3.0000 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 -10.3923 -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 -16.4545 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -3.5000 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 -15.5885 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -3.0000 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 1.7321 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 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 -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 -10.3923 -3.0000 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 -14.7224 -3.5000 0.0000 C 0 0 3 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 -3.5000 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 -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 -14.7224 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -4.5000 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 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 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 13 2 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 23 1 0 0 0 0 13 33 1 0 0 0 0 14 28 1 0 0 0 0 15 33 1 0 0 0 0 16 34 1 0 0 0 0 17 37 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 0 0 0 0 19 34 1 0 0 0 0 20 22 1 0 0 0 0 20 29 1 0 0 0 0 21 40 1 0 0 0 0 22 40 1 0 0 0 0 23 41 1 0 0 0 0 24 27 1 0 0 0 0 24 30 2 0 0 0 0 25 35 1 0 0 0 0 25 38 1 0 0 0 0 26 36 1 0 0 0 0 26 42 1 0 0 0 0 28 35 1 0 0 0 0 29 37 1 0 0 0 0 30 32 1 0 0 0 0 31 36 1 0 0 0 0 31 39 1 0 0 0 0 32 43 1 0 0 0 0 33 44 1 0 0 0 0 34 49 1 0 0 0 0 35 45 1 0 0 0 0 36 46 1 0 0 0 0 37 50 1 0 0 0 0 38 42 2 3 0 0 0 38 47 1 0 0 0 0 39 41 2 3 0 0 0 39 48 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:	762.416
LogP:	3.112
LogD:	3.375
LogS:	-4.743
# Rotatable Bonds:	23
TPSA:	157.58
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	6.055
Fsp3:	0.8
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:	-5.138
MDCK Permeability:	6.290443707257509e-05
Pgp-inhibitor:	0.787
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.976
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	96.99559783935547%
Volume Distribution (VD):	0.77
Pgp-substrate:	3.477473497390747%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.69
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.385
CYP3A4-inhibitor:	0.878
CYP3A4-substrate:	0.384

ADMET: Excretion

Clearance (CL):	8.365
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.9
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.842
Skin Sensitization:	0.638
Carcinogencity:	0.01
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC475503

Natural Product ID:	NPC475503
*Common Name:**	Bistramide K
IUPAC Name:	(6E,10E)-3,9-dihydroxy-N-[2-hydroxy-4-[3-[8-[(E)-6-hydroxy-3,5-dimethylhept-4-enyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propylamino]-3-methyl-4-oxobutyl]-4-methyldodeca-6,10-dienamide
Synonyms:	Bistramide K
Standard InCHIKey:	VBQUNUFYTUOFSU-BIKMVLIWSA-N
Standard InCHI:	InChI=1S/C40H70N2O8/c1-8-13-33(44)15-10-9-14-28(3)35(45)25-38(47)42-26-36(46)31(6)39(48)41-23-12-17-37-29(4)20-22-40(50-37)21-11-16-34(49-40)19-18-27(2)24-30(5)32(7)43/h8-10,13,24,27-29,31-37,43-46H,11-12,14-23,25-26H2,1-7H3,(H,41,48)(H,42,47)/b10-9+,13-8+,30-24+
SMILES:	CC=CC(CC=CCC(C)C(CC(=O)NCC(C(C)C(=O)NCCCC1C(CCC2(O1)CCCC(O2)CCC(C)C=C(C)C(C)O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506861
PubChem CID:	6441266
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
Others	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[537009]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.57	ug.mL-1	PMID[537009]
NPT168	Cell Line	P388	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[537009]
NPT319	Cell Line	B16	Mus musculus	IC50	=	1.9	ug.mL-1	PMID[537009]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5.6	ug.mL-1	PMID[537009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.23	ug.mL-1	PMID[537009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	49.0	%	PMID[537009]

☑ 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 NPC475503 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	82
0.1-0.2	595
0.2-0.3	3414
0.3-0.4	19572
0.4-0.5	13117
0.5-0.6	5402
0.6-0.7	411
0.7-0.8	97
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.967	High Similarity	NPC475646
0.8614	High Similarity	NPC475150
0.8462	Intermediate Similarity	NPC469865
0.8173	Intermediate Similarity	NPC473578
0.798	Intermediate Similarity	NPC189629
0.7941	Intermediate Similarity	NPC477198
0.7778	Intermediate Similarity	NPC3568
0.7778	Intermediate Similarity	NPC35269
0.7778	Intermediate Similarity	NPC256570
0.7778	Intermediate Similarity	NPC262312
0.7778	Intermediate Similarity	NPC17290
0.7778	Intermediate Similarity	NPC70323
0.7778	Intermediate Similarity	NPC23454
0.7778	Intermediate Similarity	NPC192066
0.7745	Intermediate Similarity	NPC206711
0.7745	Intermediate Similarity	NPC225978
0.7745	Intermediate Similarity	NPC255175
0.7745	Intermediate Similarity	NPC271207
0.7685	Intermediate Similarity	NPC29501
0.7653	Intermediate Similarity	NPC477865
0.7653	Intermediate Similarity	NPC209047
0.7653	Intermediate Similarity	NPC139782
0.7653	Intermediate Similarity	NPC477866
0.7653	Intermediate Similarity	NPC43074
0.7653	Intermediate Similarity	NPC242503
0.7653	Intermediate Similarity	NPC74672
0.7624	Intermediate Similarity	NPC45313
0.7624	Intermediate Similarity	NPC183449
0.7624	Intermediate Similarity	NPC197294
0.7624	Intermediate Similarity	NPC8098
0.7576	Intermediate Similarity	NPC309898
0.7576	Intermediate Similarity	NPC186840
0.7576	Intermediate Similarity	NPC182632
0.7576	Intermediate Similarity	NPC473581
0.7576	Intermediate Similarity	NPC111567
0.7576	Intermediate Similarity	NPC473604
0.7576	Intermediate Similarity	NPC15851
0.7576	Intermediate Similarity	NPC473950
0.7576	Intermediate Similarity	NPC263545
0.7576	Intermediate Similarity	NPC282705
0.7576	Intermediate Similarity	NPC475125
0.7524	Intermediate Similarity	NPC55336
0.7477	Intermediate Similarity	NPC315426
0.7426	Intermediate Similarity	NPC54961
0.7426	Intermediate Similarity	NPC282088
0.7426	Intermediate Similarity	NPC158445
0.7426	Intermediate Similarity	NPC157353
0.7426	Intermediate Similarity	NPC156782
0.74	Intermediate Similarity	NPC61894
0.74	Intermediate Similarity	NPC475603
0.7222	Intermediate Similarity	NPC475918
0.7179	Intermediate Similarity	NPC469943
0.7064	Intermediate Similarity	NPC201128
0.7041	Intermediate Similarity	NPC477199
0.701	Intermediate Similarity	NPC477385
0.701	Intermediate Similarity	NPC477390
0.7	Intermediate Similarity	NPC313658
0.7	Intermediate Similarity	NPC316138
0.6972	Remote Similarity	NPC74035
0.6931	Remote Similarity	NPC470284
0.6931	Remote Similarity	NPC316186
0.6917	Remote Similarity	NPC469494
0.6885	Remote Similarity	NPC329919
0.6885	Remote Similarity	NPC477793
0.6875	Remote Similarity	NPC474891
0.6852	Remote Similarity	NPC175531
0.6842	Remote Similarity	NPC268327
0.6842	Remote Similarity	NPC273215
0.6842	Remote Similarity	NPC295444
0.6813	Remote Similarity	NPC291196
0.6813	Remote Similarity	NPC103712
0.6807	Remote Similarity	NPC469515
0.6792	Remote Similarity	NPC195645
0.6792	Remote Similarity	NPC165332
0.6792	Remote Similarity	NPC180722
0.6786	Remote Similarity	NPC476034
0.6786	Remote Similarity	NPC474969
0.6768	Remote Similarity	NPC228638
0.6733	Remote Similarity	NPC477389
0.6733	Remote Similarity	NPC477387
0.6731	Remote Similarity	NPC472199
0.6731	Remote Similarity	NPC472197
0.6702	Remote Similarity	NPC288086
0.67	Remote Similarity	NPC476523
0.6696	Remote Similarity	NPC279383
0.6696	Remote Similarity	NPC250187
0.6667	Remote Similarity	NPC109406
0.6667	Remote Similarity	NPC477386
0.6667	Remote Similarity	NPC199382
0.6667	Remote Similarity	NPC472196
0.6667	Remote Similarity	NPC477388
0.6667	Remote Similarity	NPC314361
0.6667	Remote Similarity	NPC472195
0.6667	Remote Similarity	NPC238090
0.6638	Remote Similarity	NPC475988
0.6634	Remote Similarity	NPC471494
0.6607	Remote Similarity	NPC135216
0.6607	Remote Similarity	NPC101106
0.6606	Remote Similarity	NPC64348
0.6604	Remote Similarity	NPC5418
0.6604	Remote Similarity	NPC470283
0.6604	Remote Similarity	NPC159698
0.6604	Remote Similarity	NPC472198
0.6602	Remote Similarity	NPC248312
0.6579	Remote Similarity	NPC133625
0.6571	Remote Similarity	NPC206679
0.6571	Remote Similarity	NPC476075
0.6571	Remote Similarity	NPC471324
0.6571	Remote Similarity	NPC114172
0.6571	Remote Similarity	NPC476084
0.6525	Remote Similarity	NPC477554
0.6522	Remote Similarity	NPC305698
0.6509	Remote Similarity	NPC159092
0.6504	Remote Similarity	NPC314451
0.6504	Remote Similarity	NPC313333
0.6504	Remote Similarity	NPC313342
0.6504	Remote Similarity	NPC314512
0.65	Remote Similarity	NPC67917
0.65	Remote Similarity	NPC474312
0.65	Remote Similarity	NPC313802
0.65	Remote Similarity	NPC477515
0.65	Remote Similarity	NPC314268
0.65	Remote Similarity	NPC20072
0.6491	Remote Similarity	NPC287572
0.6491	Remote Similarity	NPC471636
0.6481	Remote Similarity	NPC175614
0.6471	Remote Similarity	NPC242233
0.6471	Remote Similarity	NPC316325
0.6471	Remote Similarity	NPC477553
0.6465	Remote Similarity	NPC100697
0.6465	Remote Similarity	NPC190008
0.6458	Remote Similarity	NPC264417
0.6458	Remote Similarity	NPC217095
0.6449	Remote Similarity	NPC256368
0.6449	Remote Similarity	NPC473314
0.6446	Remote Similarity	NPC314482
0.6442	Remote Similarity	NPC34754
0.6441	Remote Similarity	NPC471645
0.6435	Remote Similarity	NPC24389
0.6422	Remote Similarity	NPC240372
0.6422	Remote Similarity	NPC167380
0.6421	Remote Similarity	NPC55652
0.6421	Remote Similarity	NPC477085
0.6417	Remote Similarity	NPC477555
0.6415	Remote Similarity	NPC302584
0.6413	Remote Similarity	NPC259299
0.641	Remote Similarity	NPC314306
0.6408	Remote Similarity	NPC311163
0.6406	Remote Similarity	NPC119794
0.6406	Remote Similarity	NPC73829
0.64	Remote Similarity	NPC184208
0.64	Remote Similarity	NPC8538
0.64	Remote Similarity	NPC315731
0.64	Remote Similarity	NPC82799
0.6396	Remote Similarity	NPC2313
0.6396	Remote Similarity	NPC471637
0.6396	Remote Similarity	NPC475157
0.6396	Remote Similarity	NPC475655
0.6396	Remote Similarity	NPC57586
0.6396	Remote Similarity	NPC474873
0.6396	Remote Similarity	NPC154132
0.6396	Remote Similarity	NPC316250
0.6393	Remote Similarity	NPC242692
0.6392	Remote Similarity	NPC469880
0.6389	Remote Similarity	NPC189764
0.6389	Remote Similarity	NPC300710
0.6387	Remote Similarity	NPC172197
0.6387	Remote Similarity	NPC274293
0.6381	Remote Similarity	NPC159369
0.6381	Remote Similarity	NPC39290
0.6379	Remote Similarity	NPC113012
0.6379	Remote Similarity	NPC127578
0.6379	Remote Similarity	NPC122926
0.6372	Remote Similarity	NPC14537
0.6372	Remote Similarity	NPC470768
0.637	Remote Similarity	NPC214821
0.637	Remote Similarity	NPC298067
0.6364	Remote Similarity	NPC203627
0.6364	Remote Similarity	NPC234542
0.6364	Remote Similarity	NPC139712
0.6364	Remote Similarity	NPC475653
0.6357	Remote Similarity	NPC78189
0.6346	Remote Similarity	NPC477959
0.6346	Remote Similarity	NPC86005
0.6346	Remote Similarity	NPC471056
0.6346	Remote Similarity	NPC471055
0.6341	Remote Similarity	NPC472458
0.6339	Remote Similarity	NPC247060
0.6339	Remote Similarity	NPC50815
0.6337	Remote Similarity	NPC39966
0.6337	Remote Similarity	NPC224072
0.6333	Remote Similarity	NPC6531
0.633	Remote Similarity	NPC173329
0.633	Remote Similarity	NPC288350
0.633	Remote Similarity	NPC90583
0.633	Remote Similarity	NPC121857
0.633	Remote Similarity	NPC255410
0.6328	Remote Similarity	NPC475472
0.6328	Remote Similarity	NPC139585
0.6327	Remote Similarity	NPC84360

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 NPC475503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	77
0.1-0.2	365
0.2-0.3	2831
0.3-0.4	4088
0.4-0.5	1517
0.5-0.6	238
0.6-0.7	32
0.7-0.8	2
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
0.7653	Intermediate Similarity	NPD8522	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6421	Discontinued
0.6792	Remote Similarity	NPD7839	Suspended
0.6757	Remote Similarity	NPD5357	Phase 1
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4211	Phase 1
0.6509	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8342	Approved
0.6504	Remote Similarity	NPD8340	Approved
0.6504	Remote Similarity	NPD8341	Approved
0.6504	Remote Similarity	NPD8299	Approved
0.6471	Remote Similarity	NPD7500	Approved
0.646	Remote Similarity	NPD6640	Phase 3
0.641	Remote Similarity	NPD6430	Approved
0.641	Remote Similarity	NPD6429	Approved
0.64	Remote Similarity	NPD8074	Phase 3
0.6378	Remote Similarity	NPD8390	Approved
0.6378	Remote Similarity	NPD8392	Approved
0.6378	Remote Similarity	NPD8391	Approved
0.6325	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8451	Approved
0.629	Remote Similarity	NPD7829	Approved
0.629	Remote Similarity	NPD7830	Approved
0.627	Remote Similarity	NPD8448	Approved
0.625	Remote Similarity	NPD6914	Discontinued
0.6239	Remote Similarity	NPD6420	Discontinued
0.6198	Remote Similarity	NPD7505	Discontinued
0.6186	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD3168	Discontinued
0.6148	Remote Similarity	NPD7641	Discontinued
0.614	Remote Similarity	NPD1407	Approved
0.6129	Remote Similarity	NPD8444	Approved
0.6111	Remote Similarity	NPD7983	Approved
0.608	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.608	Remote Similarity	NPD7623	Phase 3
0.6068	Remote Similarity	NPD8174	Phase 2
0.6066	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8273	Phase 1
0.6036	Remote Similarity	NPD4228	Discovery
0.6019	Remote Similarity	NPD7838	Discovery
0.6019	Remote Similarity	NPD46	Approved
0.6019	Remote Similarity	NPD6698	Approved
0.6016	Remote Similarity	NPD7746	Phase 1
0.6016	Remote Similarity	NPD7747	Phase 1
0.6	Remote Similarity	NPD8266	Approved
0.6	Remote Similarity	NPD8267	Approved
0.6	Remote Similarity	NPD8268	Approved
0.6	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8269	Approved
0.5962	Remote Similarity	NPD6695	Phase 3
0.5952	Remote Similarity	NPD6436	Phase 3
0.5917	Remote Similarity	NPD1719	Phase 1
0.5909	Remote Similarity	NPD8449	Approved
0.5909	Remote Similarity	NPD5778	Approved
0.5909	Remote Similarity	NPD5779	Approved
0.5906	Remote Similarity	NPD7642	Approved
0.5905	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7750	Discontinued
0.5882	Remote Similarity	NPD6413	Approved
0.5873	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD8450	Suspended
0.5827	Remote Similarity	NPD8080	Discontinued
0.5825	Remote Similarity	NPD7514	Phase 3
0.5825	Remote Similarity	NPD7332	Phase 2
0.5821	Remote Similarity	NPD8415	Approved
0.5818	Remote Similarity	NPD7637	Suspended
0.581	Remote Similarity	NPD7154	Phase 3
0.58	Remote Similarity	NPD8264	Approved
0.5798	Remote Similarity	NPD6406	Approved
0.5784	Remote Similarity	NPD7145	Approved
0.5773	Remote Similarity	NPD791	Approved
0.5773	Remote Similarity	NPD15	Approved
0.5769	Remote Similarity	NPD6902	Approved
0.5755	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.575	Remote Similarity	NPD8306	Approved
0.575	Remote Similarity	NPD8305	Approved
0.5748	Remote Similarity	NPD8517	Approved
0.5748	Remote Similarity	NPD8516	Approved
0.5748	Remote Similarity	NPD8513	Phase 3
0.5748	Remote Similarity	NPD8515	Approved
0.5741	Remote Similarity	NPD4250	Approved
0.5741	Remote Similarity	NPD7524	Approved
0.5741	Remote Similarity	NPD4251	Approved
0.5728	Remote Similarity	NPD6929	Approved
0.5714	Remote Similarity	NPD7522	Discontinued
0.5714	Remote Similarity	NPD5771	Approved
0.5686	Remote Similarity	NPD5776	Phase 2
0.5686	Remote Similarity	NPD6925	Approved
0.5673	Remote Similarity	NPD6930	Phase 2
0.5673	Remote Similarity	NPD6931	Approved
0.5673	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6686	Approved
0.5657	Remote Similarity	NPD3187	Discontinued
0.5648	Remote Similarity	NPD4249	Approved
0.5641	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.563	Remote Similarity	NPD7333	Discontinued
0.5612	Remote Similarity	NPD7761	Suspended
0.5612	Remote Similarity	NPD1082	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