NPASS Compound

Structure

NPC471592 OpenBabel07101719512D 87 91 0 0 1 0 0 0 0 0999 V2000 -5.6920 1.1784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9974 1.1784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5111 1.7491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1418 1.2880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3866 -1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0841 -4.9220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4761 0.2255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0674 -2.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9285 2.6459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9285 3.6243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0812 2.1568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7758 5.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6231 3.6243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1716 -3.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0984 -4.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2505 0.6271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6231 5.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4704 4.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9906 -2.4903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9175 -3.9089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7949 -4.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4644 1.5818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4685 -4.3158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5969 0.9977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4064 -4.5374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8888 -1.5744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4704 1.1784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8447 0.6892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1934 1.0478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3866 -0.7784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1679 -5.2650 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8335 -0.5124 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7758 4.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2255 -4.0023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3167 0.3350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4704 5.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8636 -2.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8108 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0812 1.1784 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7915 -5.7077 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5334 -4.0956 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9550 -1.8664 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7446 2.2445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6231 0.6892 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3052 -4.5103 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8447 -0.2892 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9271 0.1063 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4555 -1.2676 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4126 -4.6431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5393 -0.2892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2339 0.6892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9540 -4.8840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5132 -0.9934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7758 1.1784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9974 -0.7784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7985 -2.1838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7684 -5.6538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9018 -3.7958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9547 0.2140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0910 2.6150 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -8.2339 -0.2892 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.9285 0.6892 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1500 -5.4415 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8255 -3.1619 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6920 -0.7784 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8119 -0.3112 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1501 -0.2892 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0894 -2.8355 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6748 -5.2856 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.4704 2.1568 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0068 -6.2301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.3177 5.5811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6827 -2.3969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9585 3.1992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6231 -0.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9182 -3.7477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5393 0.6892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3866 1.1784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6362 -5.5853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3016 -0.4140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7758 2.1568 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9974 -1.7568 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7588 -1.9963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9823 -6.6085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8181 -4.1388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9008 1.1908 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 28 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 8 68 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 33 1 0 0 0 0 12 17 1 0 0 0 0 12 33 2 0 0 0 0 13 18 2 0 0 0 0 13 33 1 0 0 0 0 14 19 1 0 0 0 0 14 34 2 0 0 0 0 15 20 2 0 0 0 0 15 34 1 0 0 0 0 16 22 2 0 0 0 0 16 35 1 0 0 0 0 17 36 2 0 0 0 0 18 36 1 0 0 0 0 19 37 2 0 0 0 0 20 37 1 0 0 0 0 21 23 1 0 0 0 0 22 43 1 0 0 0 0 23 45 1 0 0 0 0 24 35 2 0 0 0 0 24 38 1 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 44 1 0 0 0 0 27 70 1 0 0 0 0 30 5 1 1 0 0 0 30 50 1 0 0 0 0 30 61 1 0 0 0 0 31 6 1 1 0 0 0 31 71 1 0 0 0 0 32 7 1 1 0 0 0 32 48 1 0 0 0 0 32 87 1 0 0 0 0 36 72 1 0 0 0 0 37 73 1 0 0 0 0 38 43 2 0 0 0 0 38 60 1 0 0 0 0 39 11 1 1 0 0 0 39 51 1 0 0 0 0 39 62 1 0 0 0 0 40 21 1 6 0 0 0 40 57 1 0 0 0 0 40 63 1 0 0 0 0 41 25 1 6 0 0 0 41 52 1 0 0 0 0 41 64 1 0 0 0 0 42 26 1 6 0 0 0 42 53 1 0 0 0 0 42 68 1 0 0 0 0 43 74 1 0 0 0 0 44 54 1 0 0 0 0 44 75 1 6 0 0 0 45 69 1 0 0 0 0 45 76 1 1 0 0 0 46 28 1 1 0 0 0 46 55 1 0 0 0 0 46 65 1 0 0 0 0 47 29 1 6 0 0 0 47 59 1 0 0 0 0 47 66 1 0 0 0 0 48 56 1 0 0 0 0 48 67 1 1 0 0 0 49 31 1 6 0 0 0 49 58 1 0 0 0 0 49 69 1 0 0 0 0 50 65 2 3 0 0 0 50 77 1 0 0 0 0 51 61 2 3 0 0 0 51 78 1 0 0 0 0 52 63 2 3 0 0 0 52 79 1 0 0 0 0 53 66 2 3 0 0 0 53 80 1 0 0 0 0 54 62 2 3 0 0 0 54 81 1 0 0 0 0 55 67 2 3 0 0 0 55 82 1 0 0 0 0 56 64 2 3 0 0 0 56 83 1 0 0 0 0 57 69 1 0 0 0 0 57 84 2 0 0 0 0 58 68 1 0 0 0 0 58 85 2 0 0 0 0 59 86 2 0 0 0 0 59 87 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1281.48
Volume:	1212.623
LogP:	1.419
LogD:	0.189
LogS:	-1.609
# Rotatable Bonds:	23
TPSA:	426.19
# H-Bond Aceptor:	27
# H-Bond Donor:	14
# Rings:	5
# Heavy Atoms:	28

MedChem Properties

QED Drug-Likeness Score:	0.044
Synthetic Accessibility Score:	7.953
Fsp3:	0.525
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.571
MDCK Permeability:	3.983523856732063e-05
Pgp-inhibitor:	0.197
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.964
20% Bioavailability (F20%):	0.198
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.263
Plasma Protein Binding (PPB):	60.52486801147461%
Volume Distribution (VD):	0.428
Pgp-substrate:	28.71292495727539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.027
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.789
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	1.151
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.278
Skin Sensitization:	0.031
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC471592

Natural Product ID:	NPC471592
*Common Name:**	Largamide F
IUPAC Name:	(2S)-N-[(2R)-1-[[(2S)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-[(3-bromo-4-hydroxyphenyl)methyl]-21-hydroxy-2-[(1R)-1-hydroxyethyl]-15-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]-2-[[(2R)-2,3-dihydroxypropanoyl]amino]-5-(4-hydroxyphenyl)pentanamide
Synonyms:	Largamide F
Standard InCHIKey:	MZYZCUCXNWCJKE-XBSNRCLHSA-N
Standard InCHI:	InChI=1S/C59H80BrN9O18/c1-28(2)46(65-50(77)30(5)61-51(78)39(62-54(81)44(75)27-70)11-9-10-33-12-17-36(72)18-13-33)55(82)67-48-32(7)87-59(86)47(29(3)4)66-53(80)42(26-35-16-22-43(74)38(60)24-35)68(8)58(85)49(31(6)71)69-45(76)23-21-40(57(69)84)63-52(79)41(64-56(48)83)25-34-14-19-37(73)20-15-34/h12-20,22,24,28-32,39-42,44-49,70-76H,9-11,21,23,25-27H2,1-8H3,(H,61,78)(H,62,81)(H,63,79)(H,64,83)(H,65,77)(H,66,80)(H,67,82)/t30-,31-,32-,39+,40+,41+,42+,44-,45-,46+,47+,48+,49+/m1/s1
SMILES:	OC[C@H](C(=N[C@H](C(=N[C@@H](C(=N[C@H](C(=N[C@@H]1C(=N[C@@H](Cc2ccc(cc2)O)C(=N[C@H]2CC[C@H](N(C2=O)[C@H](C(=O)N([C@H](C(=N[C@H](C(=O)O[C@@H]1C)C(C)C)O)Cc1ccc(c(c1)Br)O)C)[C@H](O)C)O)O)O)O)C(C)C)O)C)O)CCCc1ccc(cc1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL269107
PubChem CID:	44448274
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16930043]
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17328572]
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20525864]
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21473610]
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	4000.0	nM	PMID[537106]

☑ 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 NPC471592 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	248
0.1-0.2	1216
0.2-0.3	5446
0.3-0.4	12355
0.4-0.5	16395
0.5-0.6	6199
0.6-0.7	633
0.7-0.8	161
0.8-0.85	27
0.85-0.9	15
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC65714
0.8814	High Similarity	NPC45037
0.8743	High Similarity	NPC230611
0.8701	High Similarity	NPC50016
0.8667	High Similarity	NPC471526
0.8644	High Similarity	NPC473402
0.8644	High Similarity	NPC473354
0.8619	High Similarity	NPC294951
0.8588	High Similarity	NPC273755
0.8541	High Similarity	NPC248822
0.8539	High Similarity	NPC159767
0.8539	High Similarity	NPC155506
0.8508	High Similarity	NPC476321
0.8486	Intermediate Similarity	NPC473305
0.8486	Intermediate Similarity	NPC163961
0.8475	Intermediate Similarity	NPC40234
0.8466	Intermediate Similarity	NPC107938
0.8466	Intermediate Similarity	NPC294516
0.8436	Intermediate Similarity	NPC476227
0.838	Intermediate Similarity	NPC137627
0.838	Intermediate Similarity	NPC306804
0.836	Intermediate Similarity	NPC473371
0.8342	Intermediate Similarity	NPC473378
0.8342	Intermediate Similarity	NPC473407
0.8333	Intermediate Similarity	NPC26108
0.8333	Intermediate Similarity	NPC279871
0.8268	Intermediate Similarity	NPC475123
0.8268	Intermediate Similarity	NPC475204
0.8216	Intermediate Similarity	NPC471050
0.8216	Intermediate Similarity	NPC471049
0.8216	Intermediate Similarity	NPC471048
0.8197	Intermediate Similarity	NPC269750
0.8197	Intermediate Similarity	NPC194671
0.8187	Intermediate Similarity	NPC473450
0.8167	Intermediate Similarity	NPC46009
0.8132	Intermediate Similarity	NPC471165
0.8077	Intermediate Similarity	NPC248670
0.7969	Intermediate Similarity	NPC302715
0.7947	Intermediate Similarity	NPC102959
0.7935	Intermediate Similarity	NPC158277
0.7906	Intermediate Similarity	NPC61332
0.7906	Intermediate Similarity	NPC240130
0.7906	Intermediate Similarity	NPC60516
0.7826	Intermediate Similarity	NPC89831
0.7819	Intermediate Similarity	NPC473404
0.7817	Intermediate Similarity	NPC477551
0.7806	Intermediate Similarity	NPC477552
0.7806	Intermediate Similarity	NPC477550
0.7708	Intermediate Similarity	NPC96275
0.765	Intermediate Similarity	NPC63931
0.7634	Intermediate Similarity	NPC328494
0.7627	Intermediate Similarity	NPC473491
0.7581	Intermediate Similarity	NPC473693
0.7581	Intermediate Similarity	NPC471568
0.7553	Intermediate Similarity	NPC136797
0.7538	Intermediate Similarity	NPC323662
0.7527	Intermediate Similarity	NPC244336
0.7514	Intermediate Similarity	NPC61004
0.7487	Intermediate Similarity	NPC196091
0.7487	Intermediate Similarity	NPC246591
0.7486	Intermediate Similarity	NPC233702
0.7473	Intermediate Similarity	NPC302597
0.7463	Intermediate Similarity	NPC469443
0.7444	Intermediate Similarity	NPC262166
0.7436	Intermediate Similarity	NPC94862
0.7424	Intermediate Similarity	NPC328763
0.7414	Intermediate Similarity	NPC239762
0.7414	Intermediate Similarity	NPC163392
0.7405	Intermediate Similarity	NPC471053
0.7405	Intermediate Similarity	NPC471051
0.7405	Intermediate Similarity	NPC471052
0.7403	Intermediate Similarity	NPC39431
0.7401	Intermediate Similarity	NPC81026
0.7391	Intermediate Similarity	NPC471527
0.7387	Intermediate Similarity	NPC80514
0.7385	Intermediate Similarity	NPC276120
0.738	Intermediate Similarity	NPC328649
0.7363	Intermediate Similarity	NPC244509
0.7363	Intermediate Similarity	NPC476268
0.736	Intermediate Similarity	NPC64140
0.736	Intermediate Similarity	NPC174122
0.7348	Intermediate Similarity	NPC473341
0.7345	Intermediate Similarity	NPC266741
0.734	Intermediate Similarity	NPC186617
0.7333	Intermediate Similarity	NPC315542
0.733	Intermediate Similarity	NPC220060
0.733	Intermediate Similarity	NPC196243
0.731	Intermediate Similarity	NPC234069
0.7287	Intermediate Similarity	NPC209463
0.7287	Intermediate Similarity	NPC141957
0.7273	Intermediate Similarity	NPC472923
0.7273	Intermediate Similarity	NPC223207
0.7268	Intermediate Similarity	NPC477637
0.7263	Intermediate Similarity	NPC16188
0.7254	Intermediate Similarity	NPC475421
0.7253	Intermediate Similarity	NPC202198
0.7253	Intermediate Similarity	NPC122590
0.7241	Intermediate Similarity	NPC123859
0.7234	Intermediate Similarity	NPC290755
0.7234	Intermediate Similarity	NPC471771
0.7234	Intermediate Similarity	NPC304074
0.7232	Intermediate Similarity	NPC91953
0.7212	Intermediate Similarity	NPC469444
0.7211	Intermediate Similarity	NPC198254
0.7211	Intermediate Similarity	NPC274198
0.72	Intermediate Similarity	NPC6570
0.72	Intermediate Similarity	NPC127741
0.7192	Intermediate Similarity	NPC50548
0.719	Intermediate Similarity	NPC469445
0.7175	Intermediate Similarity	NPC197921
0.7175	Intermediate Similarity	NPC476989
0.7165	Intermediate Similarity	NPC119652
0.7165	Intermediate Similarity	NPC97526
0.7164	Intermediate Similarity	NPC314083
0.7158	Intermediate Similarity	NPC261934
0.7158	Intermediate Similarity	NPC5194
0.7158	Intermediate Similarity	NPC56685
0.7157	Intermediate Similarity	NPC138083
0.7151	Intermediate Similarity	NPC1390
0.7151	Intermediate Similarity	NPC62104
0.7143	Intermediate Similarity	NPC470112
0.7143	Intermediate Similarity	NPC167763
0.7143	Intermediate Similarity	NPC470903
0.7143	Intermediate Similarity	NPC144314
0.7143	Intermediate Similarity	NPC254700
0.7129	Intermediate Similarity	NPC477632
0.7129	Intermediate Similarity	NPC477638
0.7128	Intermediate Similarity	NPC32064
0.7122	Intermediate Similarity	NPC242728
0.712	Intermediate Similarity	NPC276506
0.7112	Intermediate Similarity	NPC469243
0.7098	Intermediate Similarity	NPC477462
0.7097	Intermediate Similarity	NPC197743
0.7097	Intermediate Similarity	NPC56635
0.7097	Intermediate Similarity	NPC297145
0.7094	Intermediate Similarity	NPC149962
0.7088	Intermediate Similarity	NPC2501
0.7081	Intermediate Similarity	NPC219350
0.7081	Intermediate Similarity	NPC194699
0.7079	Intermediate Similarity	NPC473941
0.7074	Intermediate Similarity	NPC241794
0.7071	Intermediate Similarity	NPC299806
0.7068	Intermediate Similarity	NPC280022
0.7042	Intermediate Similarity	NPC326027
0.7039	Intermediate Similarity	NPC469360
0.7039	Intermediate Similarity	NPC176226
0.7028	Intermediate Similarity	NPC326333
0.7022	Intermediate Similarity	NPC476259
0.7021	Intermediate Similarity	NPC475544
0.7017	Intermediate Similarity	NPC314358
0.7016	Intermediate Similarity	NPC63040
0.7016	Intermediate Similarity	NPC473502
0.7011	Intermediate Similarity	NPC162104
0.701	Intermediate Similarity	NPC329295
0.701	Intermediate Similarity	NPC164608
0.7	Intermediate Similarity	NPC22883
0.7	Intermediate Similarity	NPC210377
0.7	Intermediate Similarity	NPC5719
0.7	Intermediate Similarity	NPC217804
0.6995	Remote Similarity	NPC227953
0.6986	Remote Similarity	NPC81845
0.6978	Remote Similarity	NPC135121
0.6971	Remote Similarity	NPC473724
0.6963	Remote Similarity	NPC15068
0.6963	Remote Similarity	NPC25539
0.6961	Remote Similarity	NPC313867
0.6961	Remote Similarity	NPC316008
0.6957	Remote Similarity	NPC471337
0.6948	Remote Similarity	NPC277306
0.6948	Remote Similarity	NPC469442
0.6947	Remote Similarity	NPC191863
0.6947	Remote Similarity	NPC133470
0.6947	Remote Similarity	NPC289776
0.6931	Remote Similarity	NPC29531
0.6906	Remote Similarity	NPC315283
0.6906	Remote Similarity	NPC314388
0.6901	Remote Similarity	NPC295795
0.6898	Remote Similarity	NPC473580
0.6897	Remote Similarity	NPC477526
0.689	Remote Similarity	NPC311357
0.6887	Remote Similarity	NPC478005
0.6878	Remote Similarity	NPC287757
0.6878	Remote Similarity	NPC319320
0.6875	Remote Similarity	NPC257390
0.6872	Remote Similarity	NPC475532
0.6869	Remote Similarity	NPC153554
0.6868	Remote Similarity	NPC477217
0.6868	Remote Similarity	NPC201244
0.6863	Remote Similarity	NPC477631
0.6851	Remote Similarity	NPC161069
0.6849	Remote Similarity	NPC478007
0.6847	Remote Similarity	NPC477636
0.6839	Remote Similarity	NPC319766
0.6837	Remote Similarity	NPC165285
0.6837	Remote Similarity	NPC17698
0.6836	Remote Similarity	NPC244866
0.6833	Remote Similarity	NPC268841
0.6833	Remote Similarity	NPC46098
0.6833	Remote Similarity	NPC307357
0.6832	Remote Similarity	NPC4910

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 NPC471592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	505
0.2-0.3	1002
0.3-0.4	2254
0.4-0.5	3295
0.5-0.6	1804
0.6-0.7	138
0.7-0.8	1
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
0.7189	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7811	Phase 3
0.7157	Intermediate Similarity	NPD7810	Phase 3
0.7039	Intermediate Similarity	NPD7978	Discontinued
0.7031	Intermediate Similarity	NPD7608	Discontinued
0.6978	Remote Similarity	NPD8323	Discontinued
0.6968	Remote Similarity	NPD8019	Approved
0.6963	Remote Similarity	NPD8303	Discontinued
0.6791	Remote Similarity	NPD7131	Phase 3
0.6722	Remote Similarity	NPD8172	Phase 2
0.6722	Remote Similarity	NPD8173	Phase 2
0.6718	Remote Similarity	NPD7484	Phase 3
0.6718	Remote Similarity	NPD7485	Phase 3
0.6684	Remote Similarity	NPD8417	Discontinued
0.665	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3136	Phase 2
0.6615	Remote Similarity	NPD7495	Discontinued
0.6612	Remote Similarity	NPD7450	Phase 2
0.6611	Remote Similarity	NPD6346	Approved
0.6569	Remote Similarity	NPD6853	Approved
0.6569	Remote Similarity	NPD6851	Approved
0.6566	Remote Similarity	NPD5137	Approved
0.6564	Remote Similarity	NPD8031	Discontinued
0.6552	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD8315	Phase 1
0.6477	Remote Similarity	NPD4659	Approved
0.6474	Remote Similarity	NPD7303	Discontinued
0.6471	Remote Similarity	NPD6676	Phase 2
0.6471	Remote Similarity	NPD3400	Discontinued
0.6452	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.644	Remote Similarity	NPD7523	Phase 3
0.6429	Remote Similarity	NPD8265	Approved
0.6417	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD8356	Approved
0.6406	Remote Similarity	NPD8161	Suspended
0.6404	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4103	Phase 2
0.6396	Remote Similarity	NPD8070	Approved
0.6392	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD8430	Approved
0.6373	Remote Similarity	NPD6297	Approved
0.6364	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6681	Discovery
0.635	Remote Similarity	NPD4652	Approved
0.6348	Remote Similarity	NPD3125	Approved
0.6345	Remote Similarity	NPD8351	Phase 2
0.6327	Remote Similarity	NPD7972	Discontinued
0.6313	Remote Similarity	NPD2098	Approved
0.6302	Remote Similarity	NPD7613	Discontinued
0.6301	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD5745	Approved
0.6279	Remote Similarity	NPD7565	Approved
0.6275	Remote Similarity	NPD5312	Approved
0.6275	Remote Similarity	NPD5313	Approved
0.6268	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD8162	Phase 2
0.6267	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5120	Approved
0.625	Remote Similarity	NPD5121	Approved
0.625	Remote Similarity	NPD5119	Approved
0.625	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD5484	Approved
0.6244	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD5485	Approved
0.6244	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD8025	Phase 2
0.6231	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD2888	Approved
0.6219	Remote Similarity	NPD2017	Approved
0.6219	Remote Similarity	NPD2889	Approved
0.6219	Remote Similarity	NPD2890	Approved
0.6218	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD2097	Approved
0.6209	Remote Similarity	NPD5201	Approved
0.6209	Remote Similarity	NPD4620	Approved
0.6209	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD4617	Approved
0.6209	Remote Similarity	NPD5203	Approved
0.6202	Remote Similarity	NPD7280	Phase 3
0.6202	Remote Similarity	NPD7281	Phase 3
0.6196	Remote Similarity	NPD7715	Approved
0.6196	Remote Similarity	NPD7714	Approved
0.6188	Remote Similarity	NPD7451	Discontinued
0.6178	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5746	Approved
0.6175	Remote Similarity	NPD9718	Approved
0.617	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD2904	Discontinued
0.6166	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6677	Suspended
0.6141	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD1330	Phase 2
0.6138	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD8076	Discontinued
0.6135	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD5967	Approved
0.6129	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD2575	Approved
0.6124	Remote Similarity	NPD5035	Approved
0.6122	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD5037	Approved
0.6114	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD5038	Approved
0.6111	Remote Similarity	NPD7011	Discontinued
0.6106	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6504	Approved
0.6103	Remote Similarity	NPD6505	Approved
0.6101	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD3879	Approved
0.6089	Remote Similarity	NPD5823	Approved
0.6085	Remote Similarity	NPD8106	Phase 2
0.6082	Remote Similarity	NPD3536	Discontinued
0.608	Remote Similarity	NPD5772	Approved
0.608	Remote Similarity	NPD5773	Approved
0.6078	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD4955	Approved
0.6077	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD36	Approved
0.6077	Remote Similarity	NPD4954	Approved
0.6077	Remote Similarity	NPD5026	Approved
0.6077	Remote Similarity	NPD5034	Approved
0.6077	Remote Similarity	NPD5028	Approved
0.6073	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.607	Remote Similarity	NPD5218	Approved
0.607	Remote Similarity	NPD5219	Approved
0.6067	Remote Similarity	NPD5723	Approved
0.6066	Remote Similarity	NPD5036	Approved
0.6064	Remote Similarity	NPD3552	Approved
0.6064	Remote Similarity	NPD3554	Approved
0.6064	Remote Similarity	NPD3555	Approved
0.6064	Remote Similarity	NPD3553	Approved
0.6064	Remote Similarity	NPD6852	Discontinued
0.6062	Remote Similarity	NPD6666	Approved
0.6062	Remote Similarity	NPD6667	Approved
0.6062	Remote Similarity	NPD7554	Discontinued
0.6059	Remote Similarity	NPD6107	Approved
0.6058	Remote Similarity	NPD5445	Approved
0.6056	Remote Similarity	NPD7617	Discontinued
0.6056	Remote Similarity	NPD2584	Suspended
0.6054	Remote Similarity	NPD7585	Approved
0.6054	Remote Similarity	NPD4621	Approved
0.6054	Remote Similarity	NPD4619	Approved
0.6053	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD6390	Discontinued
0.605	Remote Similarity	NPD7738	Approved
0.605	Remote Similarity	NPD7737	Approved
0.6044	Remote Similarity	NPD3878	Approved
0.6043	Remote Similarity	NPD8643	Discontinued
0.604	Remote Similarity	NPD6862	Phase 2
0.6039	Remote Similarity	NPD6042	Phase 2
0.6039	Remote Similarity	NPD6020	Phase 2
0.6039	Remote Similarity	NPD42	Phase 2
0.6038	Remote Similarity	NPD7683	Discontinued
0.6037	Remote Similarity	NPD7282	Approved
0.6032	Remote Similarity	NPD1753	Discontinued
0.6031	Remote Similarity	NPD7212	Phase 2
0.6031	Remote Similarity	NPD7213	Phase 3
0.603	Remote Similarity	NPD7577	Discontinued
0.6029	Remote Similarity	NPD5030	Phase 2
0.6029	Remote Similarity	NPD4010	Discontinued
0.6029	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD8059	Phase 3
0.6026	Remote Similarity	NPD4086	Phase 1
0.6026	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD6073	Approved
0.601	Remote Similarity	NPD6502	Phase 2
0.601	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5190	Phase 2
0.6009	Remote Similarity	NPD7583	Approved
0.6009	Remote Similarity	NPD4435	Approved
0.6	Remote Similarity	NPD5968	Phase 3
0.6	Remote Similarity	NPD5032	Approved
0.6	Remote Similarity	NPD7447	Phase 1
0.6	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6255	Approved
0.6	Remote Similarity	NPD6254	Approved
0.6	Remote Similarity	NPD6256	Approved
0.6	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7939	Discontinued
0.6	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD8320	Phase 1
0.5991	Remote Similarity	NPD8319	Approved
0.599	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD8416	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