NPASS Compound

Structure

NPC159767 OpenBabel07101718292D 74 78 0 0 1 0 0 0 0 0999 V2000 -0.8845 -5.0324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4074 -1.8231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0550 -1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4809 -0.1433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1985 2.5697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7544 -5.4726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5705 -4.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1138 7.9161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5168 -3.9660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0065 7.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3283 7.3387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1137 6.5556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4355 6.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3329 -3.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8335 4.6462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9893 3.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2947 3.4990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3681 2.1956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6777 4.1588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8335 2.6965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0472 4.1187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1206 2.8153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0569 4.7802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8577 -0.4197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6979 4.2131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8040 0.5536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1450 4.6462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9501 1.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4355 5.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1246 -1.1628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8011 0.5555 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3283 5.9782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9893 4.1588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4551 2.5374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6777 3.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9601 3.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0416 -0.9529 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1007 5.6350 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3008 4.1588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0372 1.6398 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6500 4.4319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2792 -2.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5409 4.3606 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6201 1.0868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9114 -0.2116 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3784 1.3410 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1718 -0.5127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6810 4.9113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5498 0.7955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6695 2.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0696 5.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0902 3.5621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9381 -0.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0953 -1.9263 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1495 5.4218 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6426 3.2458 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8146 0.1553 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1181 0.4606 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2241 2.5965 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9512 5.1117 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5220 2.6965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7126 4.3966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4094 -2.0193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1090 3.5683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4899 0.6467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5664 2.0602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3557 -1.0459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3213 5.6464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3023 0.1758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6351 2.1375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3349 6.4658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0206 3.8531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8308 -1.2342 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 6 1 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 5 59 1 0 0 0 0 6 7 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 32 2 0 0 0 0 13 32 1 0 0 0 0 14 42 1 0 0 0 0 15 19 1 0 0 0 0 15 33 2 0 0 0 0 16 20 2 0 0 0 0 16 33 1 0 0 0 0 17 21 1 0 0 0 0 17 34 2 0 0 0 0 18 22 2 0 0 0 0 18 34 1 0 0 0 0 19 35 2 0 0 0 0 20 35 1 0 0 0 0 21 36 2 0 0 0 0 22 36 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 43 1 0 0 0 0 26 44 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 29 32 1 0 0 0 0 31 4 1 6 0 0 0 31 46 1 0 0 0 0 31 74 1 0 0 0 0 35 61 1 0 0 0 0 36 62 1 0 0 0 0 37 24 1 1 0 0 0 37 47 1 0 0 0 0 37 54 1 0 0 0 0 38 23 1 1 0 0 0 38 51 1 0 0 0 0 38 55 1 0 0 0 0 39 27 1 1 0 0 0 39 48 1 0 0 0 0 39 56 1 0 0 0 0 40 28 1 1 0 0 0 40 49 1 0 0 0 0 40 59 1 0 0 0 0 41 29 1 1 0 0 0 41 52 1 0 0 0 0 41 60 1 0 0 0 0 42 54 2 3 0 0 0 42 63 1 0 0 0 0 43 60 1 0 0 0 0 43 64 1 6 0 0 0 44 65 2 0 0 0 0 44 66 1 0 0 0 0 45 30 1 1 0 0 0 45 53 1 0 0 0 0 45 57 1 0 0 0 0 46 50 1 0 0 0 0 46 58 1 6 0 0 0 47 58 2 3 0 0 0 47 67 1 0 0 0 0 48 55 2 3 0 0 0 48 68 1 0 0 0 0 49 57 2 3 0 0 0 49 69 1 0 0 0 0 50 56 2 3 0 0 0 50 70 1 0 0 0 0 51 60 1 0 0 0 0 51 71 2 0 0 0 0 52 59 1 0 0 0 0 52 72 2 0 0 0 0 53 73 2 0 0 0 0 53 74 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1027.49
Volume:	1035.046
LogP:	2.767
LogD:	0.976
LogS:	-2.837
# Rotatable Bonds:	19
TPSA:	313.9
# H-Bond Aceptor:	21
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.069
Synthetic Accessibility Score:	6.819
Fsp3:	0.491
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:	-6.755
MDCK Permeability:	7.990423000592273e-06
Pgp-inhibitor:	0.016
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.846
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	68.70069122314453%
Volume Distribution (VD):	0.458
Pgp-substrate:	10.848036766052246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.03
CYP2C9-inhibitor:	0.373
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.251
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	3.973
Half-life (T1/2):	0.921

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.68
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.231
Carcinogencity:	0.166
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.307

Download Data

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

Natural Product: NPC159767

Natural Product ID:	NPC159767
*Common Name:**	Micropeptin C
IUPAC Name:	(4S)-5-[[(2S,5S,8S,11R,12S,15S,18S,21R)-2-benzyl-21-hydroxy-5,15-bis[(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]-4-(hexanoylamino)-5-oxopentanoic acid
Synonyms:	Micropeptin C
Standard InCHIKey:	IXBOOEYQWFLNRB-XZZJZNPNSA-N
Standard InCHI:	InChI=1S/C53H69N7O14/c1-6-7-9-14-42(63)54-37(24-26-44(65)66)47(67)58-46-31(4)74-53(73)45(30(2)3)57-49(69)40(28-34-17-21-36(62)22-18-34)59(5)52(72)41(29-32-12-10-8-11-13-32)60-43(64)25-23-38(51(60)71)55-48(68)39(56-50(46)70)27-33-15-19-35(61)20-16-33/h8,10-13,15-22,30-31,37-41,43,45-46,61-62,64H,6-7,9,14,23-29H2,1-5H3,(H,54,63)(H,55,68)(H,56,70)(H,57,69)(H,58,67)(H,65,66)/t31-,37+,38+,39+,40+,41+,43-,45+,46+/m1/s1
SMILES:	CCCCCC(=N[C@@H](CCC(=O)O)C(=N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N=C([C@H](Cc2ccc(cc2)O)N(C)C(=O)[C@H](Cc2ccccc2)N2[C@@H](CC[C@@H](C2=O)N=C([C@H](Cc2ccc(cc2)O)N=C1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL540722
PubChem CID:	42638462
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
NPO3288.1	Microcystis aeruginosa	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19260658]

☑ 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	=	1.1	ug.mL-1	PMID[464475]

☑ 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 NPC159767 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	193
0.1-0.2	993
0.2-0.3	3517
0.3-0.4	12831
0.4-0.5	9692
0.5-0.6	13853
0.6-0.7	1181
0.7-0.8	335
0.8-0.85	55
0.85-0.9	24
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC155506
0.9747	High Similarity	NPC473402
0.9745	High Similarity	NPC230611
0.9679	High Similarity	NPC294516
0.9679	High Similarity	NPC107938
0.956	High Similarity	NPC306804
0.9444	High Similarity	NPC45037
0.9437	High Similarity	NPC137627
0.9379	High Similarity	NPC476227
0.9379	High Similarity	NPC279871
0.9333	High Similarity	NPC294951
0.9325	High Similarity	NPC194671
0.9325	High Similarity	NPC269750
0.9317	High Similarity	NPC273755
0.9313	High Similarity	NPC40234
0.9259	High Similarity	NPC473354
0.9193	High Similarity	NPC46009
0.9157	High Similarity	NPC471526
0.9085	High Similarity	NPC50016
0.9059	High Similarity	NPC473305
0.9059	High Similarity	NPC163961
0.8982	High Similarity	NPC476321
0.8957	High Similarity	NPC475123
0.8957	High Similarity	NPC475204
0.8909	High Similarity	NPC26108
0.8876	High Similarity	NPC471050
0.8876	High Similarity	NPC471048
0.8876	High Similarity	NPC471049
0.8786	High Similarity	NPC473407
0.8786	High Similarity	NPC473378
0.8757	High Similarity	NPC473404
0.8728	High Similarity	NPC240130
0.8728	High Similarity	NPC61332
0.858	High Similarity	NPC302715
0.8571	High Similarity	NPC471165
0.8553	High Similarity	NPC233702
0.8539	High Similarity	NPC471592
0.8452	Intermediate Similarity	NPC89831
0.8402	Intermediate Similarity	NPC248670
0.8385	Intermediate Similarity	NPC473341
0.8373	Intermediate Similarity	NPC63931
0.8371	Intermediate Similarity	NPC65714
0.8353	Intermediate Similarity	NPC158277
0.8302	Intermediate Similarity	NPC16188
0.8278	Intermediate Similarity	NPC473371
0.8274	Intermediate Similarity	NPC328649
0.8272	Intermediate Similarity	NPC262166
0.8269	Intermediate Similarity	NPC239762
0.8269	Intermediate Similarity	NPC163392
0.8263	Intermediate Similarity	NPC223207
0.8249	Intermediate Similarity	NPC102959
0.8239	Intermediate Similarity	NPC81026
0.8214	Intermediate Similarity	NPC471771
0.8214	Intermediate Similarity	NPC61004
0.8214	Intermediate Similarity	NPC290755
0.8214	Intermediate Similarity	NPC304074
0.8202	Intermediate Similarity	NPC60516
0.8202	Intermediate Similarity	NPC64140
0.8202	Intermediate Similarity	NPC174122
0.8198	Intermediate Similarity	NPC196243
0.8176	Intermediate Similarity	NPC266741
0.8166	Intermediate Similarity	NPC302597
0.8166	Intermediate Similarity	NPC141957
0.816	Intermediate Similarity	NPC202198
0.8148	Intermediate Similarity	NPC473491
0.8146	Intermediate Similarity	NPC234069
0.814	Intermediate Similarity	NPC136797
0.811	Intermediate Similarity	NPC39431
0.8103	Intermediate Similarity	NPC475421
0.8098	Intermediate Similarity	NPC477551
0.8095	Intermediate Similarity	NPC471051
0.8095	Intermediate Similarity	NPC471052
0.8095	Intermediate Similarity	NPC471053
0.8084	Intermediate Similarity	NPC469243
0.807	Intermediate Similarity	NPC198254
0.807	Intermediate Similarity	NPC274198
0.805	Intermediate Similarity	NPC91953
0.8047	Intermediate Similarity	NPC472923
0.8024	Intermediate Similarity	NPC244336
0.7989	Intermediate Similarity	NPC477550
0.7989	Intermediate Similarity	NPC94862
0.7989	Intermediate Similarity	NPC477552
0.7989	Intermediate Similarity	NPC50548
0.7987	Intermediate Similarity	NPC476989
0.7987	Intermediate Similarity	NPC197921
0.7978	Intermediate Similarity	NPC315542
0.7976	Intermediate Similarity	NPC475544
0.7967	Intermediate Similarity	NPC328763
0.7967	Intermediate Similarity	NPC314083
0.7966	Intermediate Similarity	NPC167763
0.7966	Intermediate Similarity	NPC470903
0.7966	Intermediate Similarity	NPC470112
0.7965	Intermediate Similarity	NPC276506
0.7965	Intermediate Similarity	NPC196091
0.7956	Intermediate Similarity	NPC248822
0.7937	Intermediate Similarity	NPC469360
0.7935	Intermediate Similarity	NPC144314
0.791	Intermediate Similarity	NPC477637
0.7903	Intermediate Similarity	NPC242728
0.7885	Intermediate Similarity	NPC257390
0.788	Intermediate Similarity	NPC149962
0.7877	Intermediate Similarity	NPC299806
0.7877	Intermediate Similarity	NPC138083
0.7853	Intermediate Similarity	NPC32064
0.7844	Intermediate Similarity	NPC244509
0.7844	Intermediate Similarity	NPC473580
0.7834	Intermediate Similarity	NPC244866
0.7833	Intermediate Similarity	NPC276120
0.7831	Intermediate Similarity	NPC261934
0.7831	Intermediate Similarity	NPC122590
0.7831	Intermediate Similarity	NPC5194
0.7829	Intermediate Similarity	NPC164608
0.7824	Intermediate Similarity	NPC241794
0.7807	Intermediate Similarity	NPC469443
0.7796	Intermediate Similarity	NPC323662
0.7791	Intermediate Similarity	NPC254700
0.7765	Intermediate Similarity	NPC471527
0.776	Intermediate Similarity	NPC477526
0.7754	Intermediate Similarity	NPC123859
0.7751	Intermediate Similarity	NPC56635
0.7746	Intermediate Similarity	NPC473502
0.7738	Intermediate Similarity	NPC476268
0.773	Intermediate Similarity	NPC477632
0.773	Intermediate Similarity	NPC477638
0.7725	Intermediate Similarity	NPC56685
0.7716	Intermediate Similarity	NPC161069
0.7714	Intermediate Similarity	NPC328494
0.7713	Intermediate Similarity	NPC473450
0.7706	Intermediate Similarity	NPC287757
0.7706	Intermediate Similarity	NPC319320
0.7705	Intermediate Similarity	NPC29531
0.7701	Intermediate Similarity	NPC186617
0.7701	Intermediate Similarity	NPC280022
0.7697	Intermediate Similarity	NPC119652
0.7697	Intermediate Similarity	NPC97526
0.7688	Intermediate Similarity	NPC6570
0.7688	Intermediate Similarity	NPC127741
0.7657	Intermediate Similarity	NPC471568
0.7657	Intermediate Similarity	NPC473693
0.7654	Intermediate Similarity	NPC153554
0.7651	Intermediate Similarity	NPC2501
0.7644	Intermediate Similarity	NPC209463
0.764	Intermediate Similarity	NPC242159
0.764	Intermediate Similarity	NPC313694
0.7634	Intermediate Similarity	NPC471563
0.7634	Intermediate Similarity	NPC59827
0.7634	Intermediate Similarity	NPC184933
0.7622	Intermediate Similarity	NPC209509
0.7596	Intermediate Similarity	NPC4910
0.7572	Intermediate Similarity	NPC133470
0.7572	Intermediate Similarity	NPC289776
0.7572	Intermediate Similarity	NPC191863
0.7571	Intermediate Similarity	NPC475532
0.7565	Intermediate Similarity	NPC220060
0.7561	Intermediate Similarity	NPC476978
0.7561	Intermediate Similarity	NPC52748
0.753	Intermediate Similarity	NPC135121
0.753	Intermediate Similarity	NPC138775
0.7528	Intermediate Similarity	NPC17698
0.7528	Intermediate Similarity	NPC165285
0.7526	Intermediate Similarity	NPC469444
0.7515	Intermediate Similarity	NPC477217
0.7515	Intermediate Similarity	NPC201244
0.7515	Intermediate Similarity	NPC5620
0.7513	Intermediate Similarity	NPC477527
0.75	Intermediate Similarity	NPC477639
0.75	Intermediate Similarity	NPC62104
0.75	Intermediate Similarity	NPC329731
0.75	Intermediate Similarity	NPC1390
0.7485	Intermediate Similarity	NPC471821
0.7485	Intermediate Similarity	NPC471820
0.747	Intermediate Similarity	NPC262077
0.747	Intermediate Similarity	NPC314358
0.7468	Intermediate Similarity	NPC469666
0.7468	Intermediate Similarity	NPC111428
0.7468	Intermediate Similarity	NPC296712
0.7456	Intermediate Similarity	NPC162104
0.7442	Intermediate Similarity	NPC326349
0.7442	Intermediate Similarity	NPC323336
0.744	Intermediate Similarity	NPC245974
0.7438	Intermediate Similarity	NPC326966
0.7433	Intermediate Similarity	NPC477631
0.743	Intermediate Similarity	NPC477462
0.7425	Intermediate Similarity	NPC225648
0.7425	Intermediate Similarity	NPC329761
0.7411	Intermediate Similarity	NPC469445
0.741	Intermediate Similarity	NPC313867
0.741	Intermediate Similarity	NPC316008
0.7401	Intermediate Similarity	NPC129486
0.7396	Intermediate Similarity	NPC324081
0.7385	Intermediate Similarity	NPC194699
0.7385	Intermediate Similarity	NPC219350
0.7375	Intermediate Similarity	NPC255447
0.7358	Intermediate Similarity	NPC473322
0.7358	Intermediate Similarity	NPC311357
0.7349	Intermediate Similarity	NPC314388
0.7349	Intermediate Similarity	NPC315283
0.7347	Intermediate Similarity	NPC478005
0.7341	Intermediate Similarity	NPC297145
0.7341	Intermediate Similarity	NPC197743

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 NPC159767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	125
0.1-0.2	422
0.2-0.3	795
0.3-0.4	1812
0.4-0.5	2866
0.5-0.6	2434
0.6-0.7	664
0.7-0.8	32
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
0.8072	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8323	Discontinued
0.7849	Intermediate Similarity	NPD7810	Phase 3
0.7849	Intermediate Similarity	NPD7811	Phase 3
0.7811	Intermediate Similarity	NPD8019	Approved
0.7759	Intermediate Similarity	NPD7608	Discontinued
0.7725	Intermediate Similarity	NPD7131	Phase 3
0.7586	Intermediate Similarity	NPD8303	Discontinued
0.7546	Intermediate Similarity	NPD7450	Phase 2
0.75	Intermediate Similarity	NPD7495	Discontinued
0.7401	Intermediate Similarity	NPD7485	Phase 3
0.7401	Intermediate Similarity	NPD7484	Phase 3
0.7375	Intermediate Similarity	NPD3136	Phase 2
0.7362	Intermediate Similarity	NPD8173	Phase 2
0.7362	Intermediate Similarity	NPD8172	Phase 2
0.7349	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6851	Approved
0.7297	Intermediate Similarity	NPD6853	Approved
0.7289	Intermediate Similarity	NPD7978	Discontinued
0.7284	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8031	Discontinued
0.7215	Intermediate Similarity	NPD4659	Approved
0.7204	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8245	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3125	Approved
0.7168	Intermediate Similarity	NPD8315	Phase 1
0.716	Intermediate Similarity	NPD3400	Discontinued
0.7151	Intermediate Similarity	NPD7303	Discontinued
0.7135	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6346	Approved
0.711	Intermediate Similarity	NPD7523	Phase 3
0.7086	Intermediate Similarity	NPD8417	Discontinued
0.7081	Intermediate Similarity	NPD6297	Approved
0.7053	Intermediate Similarity	NPD8356	Approved
0.7052	Intermediate Similarity	NPD7613	Discontinued
0.7041	Intermediate Similarity	NPD6681	Discovery
0.7037	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5137	Approved
0.7027	Intermediate Similarity	NPD7695	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4103	Phase 2
0.7019	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8025	Phase 2
0.6985	Remote Similarity	NPD8161	Suspended
0.6977	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7715	Approved
0.697	Remote Similarity	NPD7714	Approved
0.697	Remote Similarity	NPD5745	Approved
0.6964	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2098	Approved
0.6937	Remote Similarity	NPD2584	Suspended
0.6919	Remote Similarity	NPD8430	Approved
0.6919	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1330	Phase 2
0.6909	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8351	Phase 2
0.6885	Remote Similarity	NPD4652	Approved
0.6872	Remote Similarity	NPD7972	Discontinued
0.6871	Remote Similarity	NPD7451	Discontinued
0.6862	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6390	Discontinued
0.6855	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5746	Approved
0.6845	Remote Similarity	NPD6073	Approved
0.6839	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5967	Approved
0.6833	Remote Similarity	NPD2097	Approved
0.6831	Remote Similarity	NPD2888	Approved
0.6831	Remote Similarity	NPD2890	Approved
0.6831	Remote Similarity	NPD2889	Approved
0.6831	Remote Similarity	NPD2017	Approved
0.6826	Remote Similarity	NPD5120	Approved
0.6826	Remote Similarity	NPD5119	Approved
0.6826	Remote Similarity	NPD5121	Approved
0.6824	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7011	Discontinued
0.6809	Remote Similarity	NPD5445	Approved
0.6805	Remote Similarity	NPD6294	Approved
0.6805	Remote Similarity	NPD6295	Approved
0.6789	Remote Similarity	NPD7280	Phase 3
0.6789	Remote Similarity	NPD7281	Phase 3
0.6788	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5203	Approved
0.6788	Remote Similarity	NPD5201	Approved
0.6788	Remote Similarity	NPD4617	Approved
0.6788	Remote Similarity	NPD4620	Approved
0.6786	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5823	Approved
0.6771	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5485	Approved
0.6755	Remote Similarity	NPD5484	Approved
0.6742	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6312	Discontinued
0.6728	Remote Similarity	NPD2562	Approved
0.6728	Remote Similarity	NPD2561	Approved
0.6727	Remote Similarity	NPD4177	Approved
0.6727	Remote Similarity	NPD4175	Approved
0.6726	Remote Similarity	NPD8265	Approved
0.6726	Remote Similarity	NPD5296	Approved
0.6726	Remote Similarity	NPD8416	Discontinued
0.6721	Remote Similarity	NPD6862	Phase 2
0.6706	Remote Similarity	NPD3555	Approved
0.6706	Remote Similarity	NPD3554	Approved
0.6706	Remote Similarity	NPD6852	Discontinued
0.6706	Remote Similarity	NPD3552	Approved
0.6706	Remote Similarity	NPD3553	Approved
0.6704	Remote Similarity	NPD6502	Phase 2
0.6701	Remote Similarity	NPD7617	Discontinued
0.6701	Remote Similarity	NPD7861	Discontinued
0.6687	Remote Similarity	NPD4677	Discontinued
0.6686	Remote Similarity	NPD8643	Discontinued
0.6686	Remote Similarity	NPD6666	Approved
0.6686	Remote Similarity	NPD6667	Approved
0.6667	Remote Similarity	NPD1753	Discontinued
0.6667	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5190	Phase 2
0.6667	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7213	Phase 3
0.6648	Remote Similarity	NPD7212	Phase 2
0.6648	Remote Similarity	NPD7738	Approved
0.6648	Remote Similarity	NPD7737	Approved
0.6648	Remote Similarity	NPD6088	Approved
0.6647	Remote Similarity	NPD5725	Approved
0.6647	Remote Similarity	NPD2568	Approved
0.6647	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5355	Approved
0.663	Remote Similarity	NPD7577	Discontinued
0.663	Remote Similarity	NPD5356	Approved
0.6629	Remote Similarity	NPD7427	Discontinued
0.6629	Remote Similarity	NPD1670	Discontinued
0.6627	Remote Similarity	NPD6623	Phase 3
0.6626	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5313	Approved
0.6614	Remote Similarity	NPD42	Phase 2
0.6614	Remote Similarity	NPD6042	Phase 2
0.6614	Remote Similarity	NPD4603	Phase 2
0.6614	Remote Similarity	NPD5312	Approved
0.661	Remote Similarity	NPD7447	Phase 1
0.661	Remote Similarity	NPD3536	Discontinued
0.6607	Remote Similarity	NPD4619	Approved
0.6607	Remote Similarity	NPD4621	Approved
0.6606	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4576	Approved
0.6604	Remote Similarity	NPD4574	Approved
0.66	Remote Similarity	NPD7565	Approved
0.6596	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD6746	Phase 2
0.6593	Remote Similarity	NPD5773	Approved
0.6593	Remote Similarity	NPD5772	Approved
0.659	Remote Similarity	NPD8076	Discontinued
0.659	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7720	Phase 2
0.659	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD555	Phase 2
0.6585	Remote Similarity	NPD7585	Approved
0.6584	Remote Similarity	NPD8162	Phase 2
0.6584	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6505	Approved
0.6582	Remote Similarity	NPD6504	Approved
0.658	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5557	Phase 1
0.6576	Remote Similarity	NPD8070	Approved
0.6575	Remote Similarity	NPD7110	Phase 1
0.6575	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6677	Suspended
0.6573	Remote Similarity	NPD4731	Phase 3
0.6571	Remote Similarity	NPD5481	Discontinued
0.6571	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6676	Phase 2
0.6568	Remote Similarity	NPD5747	Discontinued
0.6568	Remote Similarity	NPD6405	Approved
0.6568	Remote Similarity	NPD6407	Approved
0.6567	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3455	Phase 2
0.6552	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.655	Remote Similarity	NPD3054	Approved
0.655	Remote Similarity	NPD3052	Approved
0.6548	Remote Similarity	NPD6039	Approved
0.6548	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7583	Approved
0.6534	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7602	Clinical (unspecified phase)

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