NPASS Compound

Structure

NPC471165 OpenBabel07101719512D 71 74 0 0 1 0 0 0 0 0999 V2000 6.1157 -5.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4318 -5.7106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4215 -3.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0129 -5.2076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7707 1.9345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0868 2.0274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4825 -0.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5440 -1.6770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9407 -5.7840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4631 -2.4123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6199 -2.8991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4631 -1.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7767 -2.4123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6199 -0.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9262 1.1464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2806 1.5152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1392 2.0965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4935 2.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2602 -6.3117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4421 -6.8398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1933 -4.2059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3494 -4.9300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0902 -0.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7840 -0.0944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8547 -0.3851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2469 -5.1781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2613 -4.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9020 1.4949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6979 -0.6789 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7767 -1.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9969 0.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4228 2.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6418 -1.3352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3245 -3.7662 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5978 -4.3110 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0108 -5.3705 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2469 -0.9518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5004 -0.7539 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1384 0.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6871 -6.2250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8483 0.5227 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1376 -1.5477 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7125 -1.6259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9477 -5.1056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6280 -0.2002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2875 -1.7040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2713 -2.5122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6152 -2.8369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1365 -4.9505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8806 0.4155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3513 1.2245 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3582 -1.9947 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7479 -4.5508 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0846 -3.4678 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7985 0.3097 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9961 -0.9664 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5884 -1.8636 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0386 -5.3169 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.6357 3.7060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4297 -0.4632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2091 -0.0163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4996 -2.5760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3633 -5.9862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2674 0.5341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0038 -2.3635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2446 -2.5390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5796 -2.9707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3734 -5.7800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6156 1.3525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2541 -6.4744 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 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 8 57 1 0 0 0 0 9 70 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 30 2 0 0 0 0 14 30 1 0 0 0 0 15 17 1 0 0 0 0 15 31 2 0 0 0 0 16 18 2 0 0 0 0 16 31 1 0 0 0 0 17 32 2 0 0 0 0 18 32 1 0 0 0 0 19 20 1 0 0 0 0 20 40 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 24 38 1 0 0 0 0 25 39 1 0 0 0 0 29 7 1 1 0 0 0 29 42 1 0 0 0 0 29 71 1 0 0 0 0 32 59 1 0 0 0 0 33 25 1 1 0 0 0 33 43 1 0 0 0 0 33 52 1 0 0 0 0 34 21 1 6 0 0 0 34 48 1 0 0 0 0 34 53 1 0 0 0 0 35 22 1 6 0 0 0 35 49 1 0 0 0 0 35 54 1 0 0 0 0 36 19 1 1 0 0 0 36 44 1 0 0 0 0 36 58 1 0 0 0 0 37 23 1 6 0 0 0 37 45 1 0 0 0 0 37 57 1 0 0 0 0 38 46 1 0 0 0 0 38 60 1 6 0 0 0 39 51 2 0 0 0 0 39 61 1 0 0 0 0 40 58 1 0 0 0 0 40 70 1 1 0 0 0 41 28 1 6 0 0 0 41 50 1 0 0 0 0 41 55 1 0 0 0 0 42 47 1 0 0 0 0 42 56 1 1 0 0 0 43 56 2 3 0 0 0 43 62 1 0 0 0 0 44 53 2 3 0 0 0 44 63 1 0 0 0 0 45 55 2 3 0 0 0 45 64 1 0 0 0 0 46 52 2 3 0 0 0 46 65 1 0 0 0 0 47 54 2 3 0 0 0 47 66 1 0 0 0 0 48 57 1 0 0 0 0 48 67 2 0 0 0 0 49 58 1 0 0 0 0 49 68 2 0 0 0 0 50 69 2 0 0 0 0 50 71 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	992.52
Volume:	1001.83
LogP:	2.089
LogD:	2.121
LogS:	-2.093
# Rotatable Bonds:	17
TPSA:	309.68
# H-Bond Aceptor:	21
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.066
Synthetic Accessibility Score:	6.407
Fsp3:	0.58
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.567
MDCK Permeability:	0.0001001768177957274
Pgp-inhibitor:	0.981
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.959
20% Bioavailability (F20%):	0.663
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	63.63414001464844%
Volume Distribution (VD):	0.624
Pgp-substrate:	18.07706642150879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.441
CYP2D6-inhibitor:	0.093
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	2.337
Half-life (T1/2):	0.737

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.998
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.747
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.558
Carcinogencity:	0.153
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.241

Download Data

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

Natural Product: NPC471165

Natural Product ID:	NPC471165
*Common Name:**	(S)-N1-((3S,6S,9S,12R,13S,16S,19R,21Ar)-6-Benzyl-3,16-Diisobutyl-9-Isopropyl-19-Methoxy-5,12-Dimethyl-1,4,7,10,14,17-Hexaoxoicosahydropyrrolo[2,1-L][1,4,7,10,13,16]Oxapentaazacyclononadecin-13-Yl)-2-((R)-2-Hydroxy-3-(4-Hydroxyphenyl)Propanamido)Succinamide
IUPAC Name:	(2S)-N-[(3S,6S,7R,10S,13S,16S,19R,22R)-13-benzyl-22-methoxy-7,14-dimethyl-3,16-bis(2-methylpropyl)-2,5,9,12,15,18-hexaoxo-10-propan-2-yl-8-oxa-1,4,11,14,17-pentazabicyclo[17.3.0]docosan-6-yl]-2-[[(2R)-2-hydroxy-3-(4-hydroxyphenyl)propanoyl]amino]butanediamide
Synonyms:
Standard InCHIKey:	ZXKMRIUULRZARB-AJWWNNKFSA-N
Standard InCHI:	InChI=1S/C50H72N8O13/c1-26(2)21-34-48(67)57(8)37(23-30-13-11-10-12-14-30)45(64)55-41(28(5)6)50(69)71-29(7)42(47(66)54-35(22-27(3)4)49(68)58-36(44(63)53-34)19-20-40(58)70-9)56-43(62)33(25-39(51)61)52-46(65)38(60)24-31-15-17-32(59)18-16-31/h10-18,26-29,33-38,40-42,59-60H,19-25H2,1-9H3,(H2,51,61)(H,52,65)(H,53,63)(H,54,66)(H,55,64)(H,56,62)/t29-,33+,34+,35+,36-,37+,38-,40-,41+,42+/m1/s1
SMILES:	CO[C@@H]1CC[C@H]2N1C(=O)[C@H](CC(C)C)N=C(O)[C@@H](N=C([C@@H](N=C([C@@H](Cc1ccc(cc1)O)O)O)CC(=N)O)O)[C@@H](C)OC(=O)[C@@H](N=C([C@@H](N(C(=O)[C@@H](N=C2O)CC(C)C)C)Cc1ccccc1)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385895
PubChem CID:	73353436
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
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11000050]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374973]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Einan Reservoir in Israel	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18973386]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	water bloom of the cyanobacterium Microcystis aeruginosa	n.a.	n.a.	PMID[19650639]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	bloom material	Lake Kinneret, Israel	n.a.	PMID[22280481]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Kibbutz Geva, Israel	n.a.	PMID[23153007]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Water Reservoir near Kibbutz Hafetz Haim, Israel	n.a.	PMID[23718637]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[24261937]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24642434]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24868986]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29405714]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[29847132]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9249979]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9842728]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	16900.0	nM	PMID[476444]
NPT2	Others	Unspecified		IC50	=	45900.0	nM	PMID[476444]

☑ 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 NPC471165 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	178
0.1-0.2	945
0.2-0.3	3643
0.3-0.4	12820
0.4-0.5	12029
0.5-0.6	11464
0.6-0.7	1134
0.7-0.8	350
0.8-0.85	90
0.85-0.9	32
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9321	High Similarity	NPC50016
0.9259	High Similarity	NPC26108
0.9198	High Similarity	NPC273755
0.9193	High Similarity	NPC475123
0.9193	High Similarity	NPC475204
0.9091	High Similarity	NPC45037
0.908	High Similarity	NPC248670
0.9018	High Similarity	NPC89831
0.8963	High Similarity	NPC306804
0.8963	High Similarity	NPC137627
0.8889	High Similarity	NPC61004
0.8841	High Similarity	NPC46009
0.8841	High Similarity	NPC40234
0.8834	High Similarity	NPC107938
0.8834	High Similarity	NPC294516
0.8827	High Similarity	NPC63931
0.8812	High Similarity	NPC244336
0.8795	High Similarity	NPC473402
0.8795	High Similarity	NPC473354
0.8788	High Similarity	NPC230611
0.875	High Similarity	NPC194671
0.875	High Similarity	NPC269750
0.8742	High Similarity	NPC476268
0.8683	High Similarity	NPC476227
0.8675	High Similarity	NPC328494
0.8625	High Similarity	NPC244509
0.8608	High Similarity	NPC473491
0.8571	High Similarity	NPC155506
0.8571	High Similarity	NPC158277
0.8571	High Similarity	NPC159767
0.8571	High Similarity	NPC279871
0.8547	High Similarity	NPC294951
0.8538	High Similarity	NPC476321
0.8506	High Similarity	NPC94862
0.85	High Similarity	NPC56685
0.8494	Intermediate Similarity	NPC328649
0.8488	Intermediate Similarity	NPC471526
0.8476	Intermediate Similarity	NPC241794
0.843	Intermediate Similarity	NPC477637
0.843	Intermediate Similarity	NPC473404
0.8418	Intermediate Similarity	NPC16188
0.8409	Intermediate Similarity	NPC61332
0.8409	Intermediate Similarity	NPC240130
0.8389	Intermediate Similarity	NPC477552
0.8389	Intermediate Similarity	NPC477550
0.8385	Intermediate Similarity	NPC202198
0.8385	Intermediate Similarity	NPC122590
0.8385	Intermediate Similarity	NPC262166
0.8383	Intermediate Similarity	NPC302597
0.8371	Intermediate Similarity	NPC302715
0.8353	Intermediate Similarity	NPC477462
0.8352	Intermediate Similarity	NPC102959
0.8333	Intermediate Similarity	NPC476989
0.8333	Intermediate Similarity	NPC280022
0.8333	Intermediate Similarity	NPC471049
0.8333	Intermediate Similarity	NPC471048
0.8333	Intermediate Similarity	NPC471050
0.8324	Intermediate Similarity	NPC477632
0.8324	Intermediate Similarity	NPC477638
0.8305	Intermediate Similarity	NPC473305
0.8305	Intermediate Similarity	NPC60516
0.8305	Intermediate Similarity	NPC163961
0.8297	Intermediate Similarity	NPC477551
0.8293	Intermediate Similarity	NPC323336
0.8293	Intermediate Similarity	NPC326349
0.828	Intermediate Similarity	NPC469360
0.828	Intermediate Similarity	NPC91953
0.8268	Intermediate Similarity	NPC65714
0.8239	Intermediate Similarity	NPC81026
0.8217	Intermediate Similarity	NPC197921
0.8214	Intermediate Similarity	NPC254700
0.8208	Intermediate Similarity	NPC97526
0.8208	Intermediate Similarity	NPC119652
0.8199	Intermediate Similarity	NPC2501
0.8177	Intermediate Similarity	NPC473371
0.8176	Intermediate Similarity	NPC266741
0.8156	Intermediate Similarity	NPC473407
0.8156	Intermediate Similarity	NPC473378
0.8155	Intermediate Similarity	NPC472923
0.814	Intermediate Similarity	NPC136797
0.8132	Intermediate Similarity	NPC471592
0.8098	Intermediate Similarity	NPC233702
0.8087	Intermediate Similarity	NPC323662
0.8072	Intermediate Similarity	NPC297145
0.8072	Intermediate Similarity	NPC197743
0.807	Intermediate Similarity	NPC473693
0.807	Intermediate Similarity	NPC471568
0.807	Intermediate Similarity	NPC196091
0.8059	Intermediate Similarity	NPC209463
0.8049	Intermediate Similarity	NPC5194
0.8049	Intermediate Similarity	NPC261934
0.8025	Intermediate Similarity	NPC6570
0.8012	Intermediate Similarity	NPC186617
0.8011	Intermediate Similarity	NPC477631
0.8	Intermediate Similarity	NPC477636
0.8	Intermediate Similarity	NPC475421
0.8	Intermediate Similarity	NPC52748
0.8	Intermediate Similarity	NPC39431
0.7978	Intermediate Similarity	NPC299806
0.7976	Intermediate Similarity	NPC469243
0.7967	Intermediate Similarity	NPC328763
0.7965	Intermediate Similarity	NPC198254
0.7965	Intermediate Similarity	NPC274198
0.7927	Intermediate Similarity	NPC7817
0.7927	Intermediate Similarity	NPC475168
0.7911	Intermediate Similarity	NPC127741
0.7903	Intermediate Similarity	NPC469443
0.7892	Intermediate Similarity	NPC470902
0.7877	Intermediate Similarity	NPC315542
0.7874	Intermediate Similarity	NPC475532
0.787	Intermediate Similarity	NPC475544
0.7865	Intermediate Similarity	NPC167763
0.7865	Intermediate Similarity	NPC470903
0.7865	Intermediate Similarity	NPC470112
0.7861	Intermediate Similarity	NPC276506
0.7853	Intermediate Similarity	NPC475564
0.7853	Intermediate Similarity	NPC170302
0.7853	Intermediate Similarity	NPC475409
0.7849	Intermediate Similarity	NPC141957
0.7836	Intermediate Similarity	NPC223207
0.7831	Intermediate Similarity	NPC473341
0.7829	Intermediate Similarity	NPC165285
0.7829	Intermediate Similarity	NPC17698
0.7805	Intermediate Similarity	NPC471821
0.7805	Intermediate Similarity	NPC471820
0.7799	Intermediate Similarity	NPC64205
0.7791	Intermediate Similarity	NPC304074
0.7791	Intermediate Similarity	NPC471771
0.7791	Intermediate Similarity	NPC290755
0.7784	Intermediate Similarity	NPC196243
0.7784	Intermediate Similarity	NPC477639
0.7778	Intermediate Similarity	NPC476978
0.7771	Intermediate Similarity	NPC162104
0.7771	Intermediate Similarity	NPC476744
0.7765	Intermediate Similarity	NPC471527
0.776	Intermediate Similarity	NPC248822
0.775	Intermediate Similarity	NPC242159
0.775	Intermediate Similarity	NPC313694
0.774	Intermediate Similarity	NPC473546
0.7738	Intermediate Similarity	NPC473580
0.773	Intermediate Similarity	NPC209509
0.7711	Intermediate Similarity	NPC476743
0.7708	Intermediate Similarity	NPC478005
0.7702	Intermediate Similarity	NPC163392
0.7702	Intermediate Similarity	NPC239762
0.7701	Intermediate Similarity	NPC129486
0.7692	Intermediate Similarity	NPC96275
0.7688	Intermediate Similarity	NPC471264
0.7688	Intermediate Similarity	NPC471265
0.7688	Intermediate Similarity	NPC329295
0.7683	Intermediate Similarity	NPC314358
0.7683	Intermediate Similarity	NPC262077
0.7658	Intermediate Similarity	NPC326966
0.7656	Intermediate Similarity	NPC220060
0.7644	Intermediate Similarity	NPC473502
0.7634	Intermediate Similarity	NPC59827
0.7634	Intermediate Similarity	NPC184933
0.7633	Intermediate Similarity	NPC476741
0.7622	Intermediate Similarity	NPC316008
0.7622	Intermediate Similarity	NPC313867
0.7622	Intermediate Similarity	NPC315266
0.7619	Intermediate Similarity	NPC242728
0.7617	Intermediate Similarity	NPC469444
0.7609	Intermediate Similarity	NPC51047
0.7607	Intermediate Similarity	NPC161069
0.7606	Intermediate Similarity	NPC50548
0.7602	Intermediate Similarity	NPC1390
0.7602	Intermediate Similarity	NPC287757
0.7602	Intermediate Similarity	NPC62104
0.7602	Intermediate Similarity	NPC319320
0.7582	Intermediate Similarity	NPC138083
0.7581	Intermediate Similarity	NPC314083
0.7574	Intermediate Similarity	NPC476742
0.7572	Intermediate Similarity	NPC471053
0.7572	Intermediate Similarity	NPC471052
0.7572	Intermediate Similarity	NPC471051
0.7561	Intermediate Similarity	NPC315283
0.7561	Intermediate Similarity	NPC314388
0.7556	Intermediate Similarity	NPC153554
0.7553	Intermediate Similarity	NPC144314
0.7544	Intermediate Similarity	NPC56635
0.7541	Intermediate Similarity	NPC276120
0.753	Intermediate Similarity	NPC135121
0.7526	Intermediate Similarity	NPC473450
0.7515	Intermediate Similarity	NPC477217
0.7515	Intermediate Similarity	NPC5620
0.7515	Intermediate Similarity	NPC201244
0.7514	Intermediate Similarity	NPC64140
0.7514	Intermediate Similarity	NPC174122
0.7513	Intermediate Similarity	NPC477527
0.7513	Intermediate Similarity	NPC326027
0.75	Intermediate Similarity	NPC326333
0.75	Intermediate Similarity	NPC176226
0.75	Intermediate Similarity	NPC469445
0.75	Intermediate Similarity	NPC149962
0.75	Intermediate Similarity	NPC4910
0.7485	Intermediate Similarity	NPC476259
0.7474	Intermediate Similarity	NPC194699
0.7474	Intermediate Similarity	NPC219350
0.7474	Intermediate Similarity	NPC123859

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 NPC471165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	123
0.1-0.2	352
0.2-0.3	731
0.3-0.4	1927
0.4-0.5	3140
0.5-0.6	2273
0.6-0.7	575
0.7-0.8	27
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8405	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD8303	Discontinued
0.7826	Intermediate Similarity	NPD7978	Discontinued
0.7657	Intermediate Similarity	NPD7608	Discontinued
0.7614	Intermediate Similarity	NPD5137	Approved
0.7602	Intermediate Similarity	NPD8019	Approved
0.7595	Intermediate Similarity	NPD3136	Phase 2
0.756	Intermediate Similarity	NPD7613	Discontinued
0.7515	Intermediate Similarity	NPD7131	Phase 3
0.75	Intermediate Similarity	NPD7485	Phase 3
0.75	Intermediate Similarity	NPD7484	Phase 3
0.7469	Intermediate Similarity	NPD8172	Phase 2
0.7469	Intermediate Similarity	NPD8173	Phase 2
0.7458	Intermediate Similarity	NPD4652	Approved
0.7412	Intermediate Similarity	NPD7523	Phase 3
0.741	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7495	Discontinued
0.7391	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7303	Discontinued
0.733	Intermediate Similarity	NPD2098	Approved
0.7292	Intermediate Similarity	NPD7811	Phase 3
0.7292	Intermediate Similarity	NPD7810	Phase 3
0.7229	Intermediate Similarity	NPD7450	Phase 2
0.7216	Intermediate Similarity	NPD2097	Approved
0.7169	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5772	Approved
0.7159	Intermediate Similarity	NPD5773	Approved
0.7135	Intermediate Similarity	NPD5219	Approved
0.7135	Intermediate Similarity	NPD8031	Discontinued
0.7135	Intermediate Similarity	NPD5218	Approved
0.7118	Intermediate Similarity	NPD8323	Discontinued
0.7117	Intermediate Similarity	NPD1330	Phase 2
0.7117	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7565	Approved
0.7112	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6676	Phase 2
0.7059	Intermediate Similarity	NPD3400	Discontinued
0.7053	Intermediate Similarity	NPD7617	Discontinued
0.7044	Intermediate Similarity	NPD2584	Suspended
0.7039	Intermediate Similarity	NPD4521	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8416	Discontinued
0.7021	Intermediate Similarity	NPD6853	Approved
0.7021	Intermediate Similarity	NPD6851	Approved
0.7006	Intermediate Similarity	NPD6852	Discontinued
0.6994	Remote Similarity	NPD3536	Discontinued
0.6989	Remote Similarity	NPD8417	Discontinued
0.6988	Remote Similarity	NPD8643	Discontinued
0.6982	Remote Similarity	NPD8076	Discontinued
0.6957	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5314	Approved
0.6946	Remote Similarity	NPD6073	Approved
0.6946	Remote Similarity	NPD2568	Approved
0.6941	Remote Similarity	NPD6681	Discovery
0.6937	Remote Similarity	NPD2562	Approved
0.6937	Remote Similarity	NPD2561	Approved
0.6935	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6346	Approved
0.6923	Remote Similarity	NPD2017	Approved
0.6923	Remote Similarity	NPD2890	Approved
0.6923	Remote Similarity	NPD2889	Approved
0.6923	Remote Similarity	NPD2888	Approved
0.6919	Remote Similarity	NPD6863	Phase 2
0.6909	Remote Similarity	NPD4621	Approved
0.6909	Remote Similarity	NPD4619	Approved
0.6905	Remote Similarity	NPD3553	Approved
0.6905	Remote Similarity	NPD3554	Approved
0.6905	Remote Similarity	NPD3552	Approved
0.6905	Remote Similarity	NPD3555	Approved
0.6901	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4659	Approved
0.6886	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7281	Phase 3
0.6878	Remote Similarity	NPD7280	Phase 3
0.6875	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7972	Discontinued
0.6871	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5745	Approved
0.6864	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2575	Approved
0.6854	Remote Similarity	NPD6072	Discontinued
0.6852	Remote Similarity	NPD3125	Approved
0.6845	Remote Similarity	NPD5557	Phase 1
0.6829	Remote Similarity	NPD4177	Approved
0.6829	Remote Similarity	NPD4175	Approved
0.6826	Remote Similarity	NPD3059	Approved
0.6826	Remote Similarity	NPD3061	Approved
0.6826	Remote Similarity	NPD3062	Approved
0.6825	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4103	Phase 2
0.681	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6297	Approved
0.68	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD555	Phase 2
0.6782	Remote Similarity	NPD6666	Approved
0.6782	Remote Similarity	NPD6667	Approved
0.678	Remote Similarity	NPD8315	Phase 1
0.6768	Remote Similarity	NPD7451	Discontinued
0.6766	Remote Similarity	NPD6405	Approved
0.6766	Remote Similarity	NPD6407	Approved
0.6761	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6390	Discontinued
0.6755	Remote Similarity	NPD5485	Approved
0.6755	Remote Similarity	NPD5484	Approved
0.6753	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4738	Phase 2
0.6747	Remote Similarity	NPD5746	Approved
0.6747	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5725	Approved
0.6746	Remote Similarity	NPD3052	Approved
0.6746	Remote Similarity	NPD3054	Approved
0.6744	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3455	Phase 2
0.6738	Remote Similarity	NPD3909	Discontinued
0.673	Remote Similarity	NPD2217	Approved
0.673	Remote Similarity	NPD2218	Phase 2
0.6727	Remote Similarity	NPD5204	Approved
0.6725	Remote Similarity	NPD2239	Approved
0.6725	Remote Similarity	NPD9570	Approved
0.6725	Remote Similarity	NPD2240	Approved
0.672	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD598	Approved
0.6707	Remote Similarity	NPD2626	Approved
0.6707	Remote Similarity	NPD2159	Approved
0.6707	Remote Similarity	NPD597	Approved
0.6707	Remote Similarity	NPD2160	Approved
0.6707	Remote Similarity	NPD2627	Approved
0.6707	Remote Similarity	NPD2628	Approved
0.6707	Remote Similarity	NPD601	Approved
0.6707	Remote Similarity	NPD2625	Approved
0.6707	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6901	Phase 3
0.6705	Remote Similarity	NPD3985	Discontinued
0.6705	Remote Similarity	NPD4237	Approved
0.6705	Remote Similarity	NPD4236	Phase 3
0.6702	Remote Similarity	NPD42	Phase 2
0.6702	Remote Similarity	NPD6042	Phase 2
0.6699	Remote Similarity	NPD7827	Phase 1
0.6687	Remote Similarity	NPD2613	Approved
0.6685	Remote Similarity	NPD4557	Approved
0.6685	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2978	Approved
0.6685	Remote Similarity	NPD2977	Approved
0.6685	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2570	Approved
0.6667	Remote Similarity	NPD2571	Approved
0.6667	Remote Similarity	NPD4745	Approved
0.6667	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1136	Approved
0.6667	Remote Similarity	NPD1130	Approved
0.6667	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3089	Approved
0.6667	Remote Similarity	NPD259	Phase 1
0.6667	Remote Similarity	NPD1132	Approved
0.6667	Remote Similarity	NPD3088	Approved
0.6667	Remote Similarity	NPD3616	Approved
0.6667	Remote Similarity	NPD4746	Phase 3
0.6667	Remote Similarity	NPD3087	Approved
0.6667	Remote Similarity	NPD3615	Approved
0.6667	Remote Similarity	NPD3614	Approved
0.6667	Remote Similarity	NPD5747	Discontinued
0.6667	Remote Similarity	NPD2573	Approved
0.6667	Remote Similarity	NPD2574	Discontinued
0.6667	Remote Similarity	NPD2566	Approved
0.6667	Remote Similarity	NPD3090	Approved
0.6651	Remote Similarity	NPD8356	Approved
0.6649	Remote Similarity	NPD4435	Approved
0.6649	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3007	Approved
0.663	Remote Similarity	NPD2515	Approved
0.663	Remote Similarity	NPD7011	Discontinued
0.6629	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD826	Approved
0.6627	Remote Similarity	NPD825	Approved
0.6627	Remote Similarity	NPD6623	Phase 3
0.6618	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2517	Approved
0.661	Remote Similarity	NPD3158	Phase 1
0.661	Remote Similarity	NPD3157	Approved
0.661	Remote Similarity	NPD2874	Phase 2
0.6607	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD8430	Approved
0.6598	Remote Similarity	NPD4434	Approved
0.6592	Remote Similarity	NPD4210	Discontinued
0.6592	Remote Similarity	NPD3686	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