NPASS Compound

Structure

NPC471526 OpenBabel07101719122D 80 84 0 0 1 0 0 0 0 0999 V2000 -6.9524 1.0946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8511 -1.8071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7932 -0.3246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3434 -0.5654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6195 -3.6674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5547 0.4480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8458 -2.4415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0057 0.8549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9365 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0803 2.1026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3618 2.7641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8667 1.1497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4297 2.4725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9347 0.8581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8538 -8.8922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1648 -8.7990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3831 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5373 -1.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0900 -7.3829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2289 -1.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8000 -9.8673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1110 -9.7741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5373 0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6915 -0.9766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2724 -6.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2289 -2.4415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1393 -4.2368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0148 -3.3884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3520 0.9365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8458 -1.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7400 -0.0849 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.1826 -1.5287 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5780 -3.4801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0362 -8.3580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3831 -0.9766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2161 1.5196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9286 -10.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6915 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3262 -5.8736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3831 -2.9298 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8801 -4.6684 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1384 -0.0165 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8458 -2.4415 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6005 -2.7622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4210 -0.7849 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9204 -4.3948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.2680 -1.8711 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2969 -5.7662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3831 -3.9064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1633 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6915 -2.9298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5412 -5.1486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3211 -3.7970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7797 -1.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8426 -1.5718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5373 -2.4415 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.3732 -5.6600 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.1801 -5.3494 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.2235 -0.2284 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0746 -4.8831 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.0432 -0.3840 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -11.4552 -2.8296 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.8748 -11.2834 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8458 0.4883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2473 -1.8517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5626 -6.7059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5373 -4.3948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0558 1.0080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6915 -3.9064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8999 -5.8851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2532 -4.0885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5336 -0.4045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9712 -1.1308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9766 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9766 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5510 -2.5039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 6 61 1 0 0 0 0 7 77 1 0 0 0 0 8 31 1 0 0 0 0 9 32 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 36 2 0 0 0 0 14 36 1 0 0 0 0 15 21 1 0 0 0 0 15 34 2 0 0 0 0 16 22 2 0 0 0 0 16 34 1 0 0 0 0 17 23 1 0 0 0 0 17 35 2 0 0 0 0 18 24 2 0 0 0 0 18 35 1 0 0 0 0 19 25 1 0 0 0 0 19 34 1 0 0 0 0 20 26 1 0 0 0 0 20 35 1 0 0 0 0 21 37 2 0 0 0 0 22 37 1 0 0 0 0 23 38 2 0 0 0 0 24 38 1 0 0 0 0 27 28 1 0 0 0 0 28 44 1 0 0 0 0 29 36 1 0 0 0 0 30 78 1 0 0 0 0 31 3 1 1 0 0 0 32 4 1 6 0 0 0 33 5 1 6 0 0 0 33 46 1 0 0 0 0 33 79 1 0 0 0 0 37 63 1 0 0 0 0 38 64 1 0 0 0 0 39 25 1 1 0 0 0 39 48 1 0 0 0 0 39 57 1 0 0 0 0 40 26 1 1 0 0 0 40 49 1 0 0 0 0 40 56 1 0 0 0 0 41 27 1 1 0 0 0 41 53 1 0 0 0 0 41 58 1 0 0 0 0 42 29 1 1 0 0 0 42 50 1 0 0 0 0 42 61 1 0 0 0 0 43 30 1 1 0 0 0 43 51 1 0 0 0 0 43 77 1 0 0 0 0 44 62 1 0 0 0 0 44 65 1 6 0 0 0 45 31 1 1 0 0 0 45 55 1 0 0 0 0 45 59 1 0 0 0 0 46 52 1 0 0 0 0 46 60 1 6 0 0 0 47 32 1 1 0 0 0 47 54 1 0 0 0 0 47 62 1 0 0 0 0 48 58 2 3 0 0 0 48 66 1 0 0 0 0 49 60 2 3 0 0 0 49 67 1 0 0 0 0 50 59 2 3 0 0 0 50 68 1 0 0 0 0 51 56 2 3 0 0 0 51 69 1 0 0 0 0 52 57 2 3 0 0 0 52 70 1 0 0 0 0 53 62 1 0 0 0 0 53 71 2 0 0 0 0 54 61 1 0 0 0 0 54 72 2 0 0 0 0 55 73 2 0 0 0 0 55 79 1 0 0 0 0 74 80 1 0 0 0 0 75 80 2 0 0 0 0 76 80 2 0 0 0 0 78 80 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1137.49
Volume:	1117.154
LogP:	1.391
LogD:	1.569
LogS:	-1.084
# Rotatable Bonds:	21
TPSA:	349.43
# H-Bond Aceptor:	24
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.034
Synthetic Accessibility Score:	7.419
Fsp3:	0.527
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:	-6.415
MDCK Permeability:	7.391887265839614e-06
Pgp-inhibitor:	0.479
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.986
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	84.71826171875%
Volume Distribution (VD):	0.545
Pgp-substrate:	1.958255648612976%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.284
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.256
Half-life (T1/2):	0.5

ADMET: Toxicity

hERG Blockers:	0.122
Human Hepatotoxicity (H-HT):	0.987
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.542
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.336
Carcinogencity:	0.128
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.732

Download Data

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

Natural Product: NPC471526

Natural Product ID:	NPC471526
*Common Name:**	Oscillapeptin E
IUPAC Name:	[(2R)-3-[[(2R)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-8-[(2R)-butan-2-yl]-2-[(2S)-butan-2-yl]-21-hydroxy-15-[2-(4-hydroxyphenyl)ethyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-4-(4-hydroxyphenyl)-1-oxobutan-2-yl]amino]-2-methoxy-3-oxopropyl] hydrogen sulfate
Synonyms:	Oscillapeptin E
Standard InCHIKey:	IPSPUQFSLMOERD-FESXDSMZSA-N
Standard InCHI:	InChI=1S/C55H75N7O17S/c1-8-31(3)45-55(73)79-33(5)46(60-49(67)40(26-20-35-17-23-38(64)24-18-35)56-51(69)43(77-7)30-78-80(74,75)76)52(70)57-39(25-19-34-15-21-37(63)22-16-34)48(66)58-41-27-28-44(65)62(53(41)71)47(32(4)9-2)54(72)61(6)42(50(68)59-45)29-36-13-11-10-12-14-36/h10-18,21-24,31-33,39-47,63-65H,8-9,19-20,25-30H2,1-7H3,(H,56,69)(H,57,70)(H,58,66)(H,59,68)(H,60,67)(H,74,75,76)/t31-,32+,33-,39+,40-,41+,42+,43-,44-,45+,46+,47+/m1/s1
SMILES:	CC[C@H]([C@@H]1N=C(O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H]([C@H](CC)C)N2[C@H](O)CC[C@@H](C2=O)N=C([C@@H](N=C([C@H]([C@H](OC1=O)C)N=C([C@H](N=C([C@@H](COS(=O)(=O)O)OC)O)CCc1ccc(cc1)O)O)O)CCc1ccc(cc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254782
PubChem CID:	44448153
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
NPO32547.2	oscillatoria agardhii	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[Title]

☑ 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	=	2640.0	nM	PMID[460943]

☑ 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 NPC471526 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	206
0.1-0.2	1060
0.2-0.3	4067
0.3-0.4	12959
0.4-0.5	11959
0.5-0.6	11181
0.6-0.7	922
0.7-0.8	273
0.8-0.85	32
0.85-0.9	21
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9816	High Similarity	NPC476321
0.9586	High Similarity	NPC473378
0.9586	High Similarity	NPC473407
0.9527	High Similarity	NPC163961
0.9527	High Similarity	NPC473305
0.9509	High Similarity	NPC473354
0.9345	High Similarity	NPC471049
0.9345	High Similarity	NPC471050
0.9345	High Similarity	NPC471048
0.9337	High Similarity	NPC45037
0.9268	High Similarity	NPC230611
0.9231	High Similarity	NPC294951
0.9212	High Similarity	NPC273755
0.9157	High Similarity	NPC155506
0.9157	High Similarity	NPC159767
0.9157	High Similarity	NPC473402
0.9102	High Similarity	NPC50016
0.9085	High Similarity	NPC107938
0.9085	High Similarity	NPC294516
0.8976	High Similarity	NPC40234
0.8929	High Similarity	NPC476227
0.8869	High Similarity	NPC306804
0.8869	High Similarity	NPC137627
0.8817	High Similarity	NPC26108
0.8817	High Similarity	NPC279871
0.8814	High Similarity	NPC302715
0.88	High Similarity	NPC102959
0.875	High Similarity	NPC60516
0.8667	High Similarity	NPC471592
0.8663	High Similarity	NPC194671
0.8663	High Similarity	NPC269750
0.8639	High Similarity	NPC46009
0.8639	High Similarity	NPC475204
0.8639	High Similarity	NPC475123
0.85	High Similarity	NPC65714
0.8488	Intermediate Similarity	NPC471165
0.8452	Intermediate Similarity	NPC471052
0.8452	Intermediate Similarity	NPC471053
0.8452	Intermediate Similarity	NPC471051
0.8443	Intermediate Similarity	NPC471527
0.843	Intermediate Similarity	NPC248670
0.8407	Intermediate Similarity	NPC473371
0.8266	Intermediate Similarity	NPC89831
0.8249	Intermediate Similarity	NPC473404
0.8232	Intermediate Similarity	NPC240130
0.8232	Intermediate Similarity	NPC61332
0.8187	Intermediate Similarity	NPC63931
0.8068	Intermediate Similarity	NPC158277
0.8063	Intermediate Similarity	NPC220060
0.8033	Intermediate Similarity	NPC64140
0.8033	Intermediate Similarity	NPC174122
0.8024	Intermediate Similarity	NPC233702
0.7978	Intermediate Similarity	NPC234069
0.7976	Intermediate Similarity	NPC262166
0.7963	Intermediate Similarity	NPC163392
0.7963	Intermediate Similarity	NPC239762
0.7939	Intermediate Similarity	NPC81026
0.7923	Intermediate Similarity	NPC94862
0.7898	Intermediate Similarity	NPC196091
0.7897	Intermediate Similarity	NPC469445
0.7886	Intermediate Similarity	NPC302597
0.7879	Intermediate Similarity	NPC266741
0.787	Intermediate Similarity	NPC473341
0.7857	Intermediate Similarity	NPC473491
0.7842	Intermediate Similarity	NPC477551
0.7842	Intermediate Similarity	NPC469443
0.784	Intermediate Similarity	NPC127741
0.784	Intermediate Similarity	NPC6570
0.7835	Intermediate Similarity	NPC469444
0.7831	Intermediate Similarity	NPC477550
0.7831	Intermediate Similarity	NPC477552
0.7831	Intermediate Similarity	NPC50548
0.7829	Intermediate Similarity	NPC471771
0.7829	Intermediate Similarity	NPC290755
0.7829	Intermediate Similarity	NPC304074
0.7829	Intermediate Similarity	NPC61004
0.7824	Intermediate Similarity	NPC39431
0.7821	Intermediate Similarity	NPC196243
0.7814	Intermediate Similarity	NPC138083
0.7797	Intermediate Similarity	NPC473693
0.7797	Intermediate Similarity	NPC471568
0.779	Intermediate Similarity	NPC32064
0.7784	Intermediate Similarity	NPC16188
0.7784	Intermediate Similarity	NPC63040
0.7778	Intermediate Similarity	NPC476268
0.7778	Intermediate Similarity	NPC144314
0.7772	Intermediate Similarity	NPC276120
0.7771	Intermediate Similarity	NPC22883
0.7771	Intermediate Similarity	NPC5719
0.7771	Intermediate Similarity	NPC210377
0.7771	Intermediate Similarity	NPC217804
0.7771	Intermediate Similarity	NPC223207
0.7771	Intermediate Similarity	NPC472923
0.7753	Intermediate Similarity	NPC328494
0.7749	Intermediate Similarity	NPC242728
0.774	Intermediate Similarity	NPC186617
0.7727	Intermediate Similarity	NPC15068
0.7725	Intermediate Similarity	NPC149962
0.7717	Intermediate Similarity	NPC315542
0.7701	Intermediate Similarity	NPC248822
0.7697	Intermediate Similarity	NPC476989
0.7688	Intermediate Similarity	NPC56635
0.7684	Intermediate Similarity	NPC328649
0.7684	Intermediate Similarity	NPC141957
0.7667	Intermediate Similarity	NPC136797
0.7667	Intermediate Similarity	NPC164608
0.7661	Intermediate Similarity	NPC202198
0.7651	Intermediate Similarity	NPC91953
0.765	Intermediate Similarity	NPC477637
0.7644	Intermediate Similarity	NPC244336
0.7644	Intermediate Similarity	NPC323662
0.7638	Intermediate Similarity	NPC25539
0.7637	Intermediate Similarity	NPC475421
0.7626	Intermediate Similarity	NPC277306
0.7626	Intermediate Similarity	NPC469442
0.7604	Intermediate Similarity	NPC123859
0.76	Intermediate Similarity	NPC469243
0.76	Intermediate Similarity	NPC475544
0.7598	Intermediate Similarity	NPC276506
0.7598	Intermediate Similarity	NPC274198
0.7598	Intermediate Similarity	NPC198254
0.759	Intermediate Similarity	NPC197921
0.7584	Intermediate Similarity	NPC209463
0.7558	Intermediate Similarity	NPC5194
0.7558	Intermediate Similarity	NPC261934
0.7558	Intermediate Similarity	NPC122590
0.7553	Intermediate Similarity	NPC29531
0.7545	Intermediate Similarity	NPC469360
0.7543	Intermediate Similarity	NPC1390
0.7543	Intermediate Similarity	NPC62104
0.7542	Intermediate Similarity	NPC280022
0.7541	Intermediate Similarity	NPC97526
0.7541	Intermediate Similarity	NPC119652
0.7528	Intermediate Similarity	NPC254700
0.7526	Intermediate Similarity	NPC328763
0.7526	Intermediate Similarity	NPC314083
0.7514	Intermediate Similarity	NPC167763
0.7514	Intermediate Similarity	NPC470112
0.7514	Intermediate Similarity	NPC470903
0.7487	Intermediate Similarity	NPC477638
0.7487	Intermediate Similarity	NPC477632
0.7471	Intermediate Similarity	NPC244509
0.7471	Intermediate Similarity	NPC135121
0.7457	Intermediate Similarity	NPC56685
0.7456	Intermediate Similarity	NPC201244
0.7456	Intermediate Similarity	NPC477217
0.7439	Intermediate Similarity	NPC244866
0.7433	Intermediate Similarity	NPC299806
0.7424	Intermediate Similarity	NPC194699
0.7424	Intermediate Similarity	NPC219350
0.7412	Intermediate Similarity	NPC262077
0.741	Intermediate Similarity	NPC68865
0.7396	Intermediate Similarity	NPC471563
0.7387	Intermediate Similarity	NPC478005
0.7386	Intermediate Similarity	NPC197743
0.7386	Intermediate Similarity	NPC297145
0.7385	Intermediate Similarity	NPC473450
0.7384	Intermediate Similarity	NPC2501
0.7378	Intermediate Similarity	NPC257390
0.7371	Intermediate Similarity	NPC473580
0.736	Intermediate Similarity	NPC241794
0.733	Intermediate Similarity	NPC477526
0.733	Intermediate Similarity	NPC478007
0.7318	Intermediate Similarity	NPC289776
0.7318	Intermediate Similarity	NPC133470
0.7318	Intermediate Similarity	NPC191863
0.7312	Intermediate Similarity	NPC153554
0.731	Intermediate Similarity	NPC311357
0.7294	Intermediate Similarity	NPC52748
0.7293	Intermediate Similarity	NPC473502
0.7283	Intermediate Similarity	NPC477462
0.7263	Intermediate Similarity	NPC4910
0.726	Intermediate Similarity	NPC478008
0.7247	Intermediate Similarity	NPC287757
0.7247	Intermediate Similarity	NPC319320
0.7241	Intermediate Similarity	NPC7817
0.7241	Intermediate Similarity	NPC475168
0.7235	Intermediate Similarity	NPC161069
0.7235	Intermediate Similarity	NPC176226
0.7228	Intermediate Similarity	NPC475532
0.7225	Intermediate Similarity	NPC471820
0.7225	Intermediate Similarity	NPC471821
0.7219	Intermediate Similarity	NPC268841
0.7219	Intermediate Similarity	NPC307357
0.7219	Intermediate Similarity	NPC46098
0.7216	Intermediate Similarity	NPC184933
0.7216	Intermediate Similarity	NPC59827
0.7209	Intermediate Similarity	NPC314358
0.7206	Intermediate Similarity	NPC326027
0.7202	Intermediate Similarity	NPC477631
0.72	Intermediate Similarity	NPC162104
0.7192	Intermediate Similarity	NPC326333
0.7191	Intermediate Similarity	NPC326349
0.7191	Intermediate Similarity	NPC323336
0.7189	Intermediate Similarity	NPC17698
0.7189	Intermediate Similarity	NPC165285
0.7188	Intermediate Similarity	NPC477636
0.7184	Intermediate Similarity	NPC245974
0.7179	Intermediate Similarity	NPC329295
0.7176	Intermediate Similarity	NPC168113

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 NPC471526 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	129
0.1-0.2	428
0.2-0.3	841
0.3-0.4	1952
0.4-0.5	3135
0.5-0.6	2213
0.6-0.7	442
0.7-0.8	10
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
0.7598	Intermediate Similarity	NPD7608	Discontinued
0.7586	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8323	Discontinued
0.7345	Intermediate Similarity	NPD8019	Approved
0.7333	Intermediate Similarity	NPD8303	Discontinued
0.7333	Intermediate Similarity	NPD7810	Phase 3
0.7333	Intermediate Similarity	NPD7811	Phase 3
0.7257	Intermediate Similarity	NPD7131	Phase 3
0.7158	Intermediate Similarity	NPD7484	Phase 3
0.7158	Intermediate Similarity	NPD7485	Phase 3
0.7158	Intermediate Similarity	NPD6853	Approved
0.7158	Intermediate Similarity	NPD6851	Approved
0.7143	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7978	Discontinued
0.7108	Intermediate Similarity	NPD3136	Phase 2
0.7076	Intermediate Similarity	NPD7450	Phase 2
0.7068	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7495	Discontinued
0.7039	Intermediate Similarity	NPD8417	Discontinued
0.7024	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7303	Discontinued
0.6995	Remote Similarity	NPD8031	Discontinued
0.6982	Remote Similarity	NPD6346	Approved
0.6947	Remote Similarity	NPD6297	Approved
0.6927	Remote Similarity	NPD8315	Phase 1
0.6919	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4659	Approved
0.6821	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD2098	Approved
0.6811	Remote Similarity	NPD8070	Approved
0.6809	Remote Similarity	NPD5137	Approved
0.6807	Remote Similarity	NPD3125	Approved
0.6806	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8173	Phase 2
0.6802	Remote Similarity	NPD8172	Phase 2
0.68	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6681	Discovery
0.6776	Remote Similarity	NPD8356	Approved
0.6774	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4652	Approved
0.6739	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5745	Approved
0.6723	Remote Similarity	NPD3400	Discontinued
0.6721	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2097	Approved
0.6702	Remote Similarity	NPD2889	Approved
0.6702	Remote Similarity	NPD2890	Approved
0.6702	Remote Similarity	NPD2017	Approved
0.6702	Remote Similarity	NPD2888	Approved
0.6699	Remote Similarity	NPD8161	Suspended
0.6686	Remote Similarity	NPD5121	Approved
0.6686	Remote Similarity	NPD5119	Approved
0.6686	Remote Similarity	NPD5120	Approved
0.6685	Remote Similarity	NPD7523	Phase 3
0.6667	Remote Similarity	NPD4103	Phase 2
0.6667	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8351	Phase 2
0.6651	Remote Similarity	NPD8430	Approved
0.665	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7565	Approved
0.6648	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4620	Approved
0.6647	Remote Similarity	NPD5201	Approved
0.6647	Remote Similarity	NPD5203	Approved
0.6647	Remote Similarity	NPD4617	Approved
0.663	Remote Similarity	NPD7613	Discontinued
0.6629	Remote Similarity	NPD6676	Phase 2
0.6628	Remote Similarity	NPD7714	Approved
0.6628	Remote Similarity	NPD7715	Approved
0.6627	Remote Similarity	NPD7451	Discontinued
0.6613	Remote Similarity	NPD7738	Approved
0.6613	Remote Similarity	NPD7737	Approved
0.6608	Remote Similarity	NPD5746	Approved
0.6592	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.659	Remote Similarity	NPD8265	Approved
0.6582	Remote Similarity	NPD7280	Phase 3
0.6582	Remote Similarity	NPD7281	Phase 3
0.6575	Remote Similarity	NPD3536	Discontinued
0.657	Remote Similarity	NPD1330	Phase 2
0.657	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2904	Discontinued
0.6559	Remote Similarity	NPD5773	Approved
0.6559	Remote Similarity	NPD5772	Approved
0.6559	Remote Similarity	NPD7972	Discontinued
0.6541	Remote Similarity	NPD6677	Suspended
0.6538	Remote Similarity	NPD6390	Discontinued
0.6534	Remote Similarity	NPD1753	Discontinued
0.6533	Remote Similarity	NPD8025	Phase 2
0.6524	Remote Similarity	NPD5967	Approved
0.6522	Remote Similarity	NPD3455	Phase 2
0.6514	Remote Similarity	NPD6073	Approved
0.6513	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5723	Approved
0.6506	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5355	Approved
0.6505	Remote Similarity	NPD5356	Approved
0.65	Remote Similarity	NPD7861	Discontinued
0.6495	Remote Similarity	NPD5312	Approved
0.6495	Remote Similarity	NPD5313	Approved
0.6488	Remote Similarity	NPD2584	Suspended
0.648	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6295	Approved
0.6477	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6852	Discontinued
0.6477	Remote Similarity	NPD6294	Approved
0.6476	Remote Similarity	NPD7585	Approved
0.6474	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4619	Approved
0.6474	Remote Similarity	NPD4621	Approved
0.6471	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6667	Approved
0.6464	Remote Similarity	NPD6666	Approved
0.6462	Remote Similarity	NPD5484	Approved
0.6462	Remote Similarity	NPD5485	Approved
0.6461	Remote Similarity	NPD3656	Approved
0.6461	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD555	Phase 2
0.6455	Remote Similarity	NPD5218	Approved
0.6455	Remote Similarity	NPD5219	Approved
0.6452	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7110	Phase 1
0.6452	Remote Similarity	NPD6072	Discontinued
0.645	Remote Similarity	NPD4435	Approved
0.6444	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.644	Remote Similarity	NPD6107	Approved
0.6436	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5445	Approved
0.6429	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7583	Approved
0.6425	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2568	Approved
0.642	Remote Similarity	NPD5314	Approved
0.6417	Remote Similarity	NPD2515	Approved
0.6417	Remote Similarity	NPD7011	Discontinued
0.6417	Remote Similarity	NPD3007	Approved
0.6416	Remote Similarity	NPD4738	Phase 2
0.6412	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6042	Phase 2
0.641	Remote Similarity	NPD42	Phase 2
0.6409	Remote Similarity	NPD5241	Discontinued
0.6406	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5296	Approved
0.64	Remote Similarity	NPD4434	Approved
0.6396	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4177	Approved
0.6395	Remote Similarity	NPD4175	Approved
0.6393	Remote Similarity	NPD7447	Phase 1
0.6393	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD2562	Approved
0.6391	Remote Similarity	NPD2561	Approved
0.6387	Remote Similarity	NPD5823	Approved
0.6386	Remote Similarity	NPD6504	Approved
0.6386	Remote Similarity	NPD6505	Approved
0.6384	Remote Similarity	NPD3555	Approved
0.6384	Remote Similarity	NPD3553	Approved
0.6384	Remote Similarity	NPD3554	Approved
0.6384	Remote Similarity	NPD3552	Approved
0.6382	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5190	Phase 2
0.6377	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2626	Approved
0.6374	Remote Similarity	NPD2160	Approved
0.6374	Remote Similarity	NPD2627	Approved
0.6374	Remote Similarity	NPD2159	Approved
0.6374	Remote Similarity	NPD5295	Discontinued
0.6374	Remote Similarity	NPD2625	Approved
0.6374	Remote Similarity	NPD2628	Approved
0.6373	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD8076	Discontinued
0.6368	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2513	Approved
0.6355	Remote Similarity	NPD3879	Approved
0.6354	Remote Similarity	NPD5481	Discontinued
0.6353	Remote Similarity	NPD4677	Discontinued
0.6349	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6255	Approved
0.6346	Remote Similarity	NPD6254	Approved
0.6346	Remote Similarity	NPD6256	Approved
0.6343	Remote Similarity	NPD259	Phase 1
0.6343	Remote Similarity	NPD6407	Approved
0.6343	Remote Similarity	NPD6405	Approved
0.6339	Remote Similarity	NPD7212	Phase 2
0.6339	Remote Similarity	NPD7213	Phase 3

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