NPASS Compound

Structure

NPC294516 OpenBabel07101719512D 73 76 0 0 1 0 0 0 0 0999 V2000 0.1221 6.5346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1103 -6.5512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4332 -6.3656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4065 1.8218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0530 1.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4799 0.1432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1951 -2.5680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9913 6.9745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8069 6.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7532 5.4689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5688 4.9361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5151 3.9634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3307 3.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8309 -4.6431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9873 -3.1818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2905 -3.4966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3632 -2.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6746 -4.1560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8309 -2.6947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0425 -4.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1152 -2.8135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0562 -4.7771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8545 0.4195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6968 -4.2103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8008 -0.5533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4325 -5.0059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1436 -4.6431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9468 -1.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3254 -5.9742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1232 1.1620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8006 -0.5551 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9873 -4.1560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4508 -2.5357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6746 -3.1818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9548 -3.7744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0389 0.9523 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1000 -5.6312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2999 -4.1560 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0345 -1.6387 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6476 -4.4290 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2770 2.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5392 -4.3577 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6164 -1.0861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9102 0.2114 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3775 -1.3401 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1697 0.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6806 -4.9080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5474 -0.7950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6683 -2.2699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0683 -5.5241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0874 -3.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9374 0.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0926 1.9250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1494 -5.4182 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6415 -3.2437 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8127 -0.1552 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1160 -0.4603 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2213 -2.5948 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9493 -5.1083 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5183 -2.6947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7068 -4.3937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4078 2.0180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1069 -3.5660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4856 -0.6462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5627 -2.0588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3541 1.0452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3204 -5.6427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2994 -0.1757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6333 -2.1360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3333 -6.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0172 -3.8506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8303 1.2334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 29 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 7 58 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 41 1 0 0 0 0 14 18 1 0 0 0 0 14 32 2 0 0 0 0 15 19 2 0 0 0 0 15 32 1 0 0 0 0 16 20 1 0 0 0 0 16 33 2 0 0 0 0 17 21 2 0 0 0 0 17 33 1 0 0 0 0 18 34 2 0 0 0 0 19 34 1 0 0 0 0 20 35 2 0 0 0 0 21 35 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 42 1 0 0 0 0 25 43 1 0 0 0 0 26 29 1 0 0 0 0 27 32 1 0 0 0 0 28 33 1 0 0 0 0 31 6 1 6 0 0 0 31 45 1 0 0 0 0 31 73 1 0 0 0 0 34 60 1 0 0 0 0 35 61 1 0 0 0 0 36 23 1 1 0 0 0 36 46 1 0 0 0 0 36 53 1 0 0 0 0 37 22 1 1 0 0 0 37 50 1 0 0 0 0 37 54 1 0 0 0 0 38 27 1 1 0 0 0 38 47 1 0 0 0 0 38 55 1 0 0 0 0 39 28 1 1 0 0 0 39 48 1 0 0 0 0 39 58 1 0 0 0 0 40 26 1 1 0 0 0 40 51 1 0 0 0 0 40 59 1 0 0 0 0 41 53 2 3 0 0 0 41 62 1 0 0 0 0 42 59 1 0 0 0 0 42 63 1 6 0 0 0 43 64 2 0 0 0 0 43 65 1 0 0 0 0 44 30 1 1 0 0 0 44 52 1 0 0 0 0 44 56 1 0 0 0 0 45 49 1 0 0 0 0 45 57 1 6 0 0 0 46 57 2 3 0 0 0 46 66 1 0 0 0 0 47 54 2 3 0 0 0 47 67 1 0 0 0 0 48 56 2 3 0 0 0 48 68 1 0 0 0 0 49 55 2 3 0 0 0 49 69 1 0 0 0 0 50 59 1 0 0 0 0 50 70 2 0 0 0 0 51 58 1 0 0 0 0 51 71 2 0 0 0 0 52 72 2 0 0 0 0 52 73 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1021.54
Volume:	1034.215
LogP:	3.88
LogD:	1.578
LogS:	-2.785
# Rotatable Bonds:	21
TPSA:	313.9
# H-Bond Aceptor:	21
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.072
Synthetic Accessibility Score:	6.87
Fsp3:	0.596
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:	-6.492
MDCK Permeability:	1.0590155397949275e-05
Pgp-inhibitor:	0.124
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.918
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	67.35453033447266%
Volume Distribution (VD):	0.402
Pgp-substrate:	8.315840721130371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.298
CYP2C9-substrate:	0.99
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.26
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	4.853
Half-life (T1/2):	0.921

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.325
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.274
Carcinogencity:	0.211
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.215

Download Data

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

Natural Product: NPC294516

Natural Product ID:	NPC294516
*Common Name:**	Micropeptin F
IUPAC Name:	(4S)-5-[[(2S,5S,8S,11R,12S,15S,18S,21R)-21-hydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-4,11-dimethyl-2-(2-methylpropyl)-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-(octanoylamino)-5-oxopentanoic acid
Synonyms:	Micropeptin F
Standard InCHIKey:	LDXXBAHTNLNWIZ-WXCLYRHNSA-N
Standard InCHI:	InChI=1S/C52H75N7O14/c1-8-9-10-11-12-13-41(62)53-36(23-25-43(64)65)46(66)57-45-31(6)73-52(72)44(30(4)5)56-48(68)39(28-33-16-20-35(61)21-17-33)58(7)51(71)40(26-29(2)3)59-42(63)24-22-37(50(59)70)54-47(67)38(55-49(45)69)27-32-14-18-34(60)19-15-32/h14-21,29-31,36-40,42,44-45,60-61,63H,8-13,22-28H2,1-7H3,(H,53,62)(H,54,67)(H,55,69)(H,56,68)(H,57,66)(H,64,65)/t31-,36+,37+,38+,39+,40+,42-,44+,45+/m1/s1
SMILES:	CCCCCCCC(=N[C@H](C(=N[C@@H]1C(=N[C@@H](Cc2ccc(cc2)O)C(=N[C@H]2CC[C@H](N(C2=O)[C@H](C(=O)N([C@H](C(=N[C@H](C(=O)O[C@@H]1C)C(C)C)O)Cc1ccc(cc1)O)C)CC(C)C)O)O)O)O)CCC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL539711
PubChem CID:	42638301
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	=	1.5	ug.mL-1	PMID[468700]

☑ 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 NPC294516 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	187
0.1-0.2	962
0.2-0.3	3825
0.3-0.4	13016
0.4-0.5	10390
0.5-0.6	12826
0.6-0.7	1036
0.7-0.8	346
0.8-0.85	57
0.85-0.9	28
0.9-0.95	14
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC107938
0.9679	High Similarity	NPC155506
0.9679	High Similarity	NPC159767
0.9679	High Similarity	NPC473402
0.9677	High Similarity	NPC230611
0.9615	High Similarity	NPC273755
0.9615	High Similarity	NPC306804
0.9613	High Similarity	NPC40234
0.9554	High Similarity	NPC476227
0.949	High Similarity	NPC137627
0.9487	High Similarity	NPC46009
0.943	High Similarity	NPC473354
0.943	High Similarity	NPC279871
0.9375	High Similarity	NPC269750
0.9375	High Similarity	NPC45037
0.9375	High Similarity	NPC194671
0.9371	High Similarity	NPC50016
0.9241	High Similarity	NPC475204
0.9241	High Similarity	NPC475123
0.9141	High Similarity	NPC476321
0.9085	High Similarity	NPC471526
0.903	High Similarity	NPC294951
0.9024	High Similarity	NPC473404
0.8951	High Similarity	NPC26108
0.8916	High Similarity	NPC471050
0.8916	High Similarity	NPC471049
0.8916	High Similarity	NPC471048
0.8834	High Similarity	NPC471165
0.8765	High Similarity	NPC240130
0.8765	High Similarity	NPC163961
0.8765	High Similarity	NPC473305
0.8765	High Similarity	NPC61332
0.8713	High Similarity	NPC473407
0.8713	High Similarity	NPC473378
0.8659	High Similarity	NPC248670
0.8654	High Similarity	NPC473341
0.8613	High Similarity	NPC65714
0.8613	High Similarity	NPC302715
0.8543	High Similarity	NPC163392
0.8543	High Similarity	NPC239762
0.8535	High Similarity	NPC262166
0.8514	High Similarity	NPC473371
0.8506	High Similarity	NPC81026
0.8488	Intermediate Similarity	NPC102959
0.8466	Intermediate Similarity	NPC471592
0.8466	Intermediate Similarity	NPC61004
0.8442	Intermediate Similarity	NPC266741
0.8439	Intermediate Similarity	NPC60516
0.8415	Intermediate Similarity	NPC302597
0.8408	Intermediate Similarity	NPC473491
0.8405	Intermediate Similarity	NPC63931
0.8383	Intermediate Similarity	NPC158277
0.8373	Intermediate Similarity	NPC89831
0.8365	Intermediate Similarity	NPC39431
0.8354	Intermediate Similarity	NPC233702
0.8333	Intermediate Similarity	NPC16188
0.8312	Intermediate Similarity	NPC91953
0.8293	Intermediate Similarity	NPC472923
0.8272	Intermediate Similarity	NPC244336
0.8247	Intermediate Similarity	NPC476989
0.8247	Intermediate Similarity	NPC197921
0.8194	Intermediate Similarity	NPC469360
0.8187	Intermediate Similarity	NPC202198
0.8182	Intermediate Similarity	NPC248822
0.814	Intermediate Similarity	NPC477637
0.8129	Intermediate Similarity	NPC475421
0.8122	Intermediate Similarity	NPC477551
0.8121	Intermediate Similarity	NPC471053
0.8121	Intermediate Similarity	NPC471052
0.8121	Intermediate Similarity	NPC471051
0.811	Intermediate Similarity	NPC469243
0.8095	Intermediate Similarity	NPC274198
0.8095	Intermediate Similarity	NPC198254
0.8086	Intermediate Similarity	NPC244509
0.8075	Intermediate Similarity	NPC5194
0.8075	Intermediate Similarity	NPC261934
0.8072	Intermediate Similarity	NPC223207
0.8024	Intermediate Similarity	NPC290755
0.8024	Intermediate Similarity	NPC471771
0.8024	Intermediate Similarity	NPC304074
0.8024	Intermediate Similarity	NPC254700
0.8023	Intermediate Similarity	NPC64140
0.8023	Intermediate Similarity	NPC174122
0.8022	Intermediate Similarity	NPC469443
0.8012	Intermediate Similarity	NPC196243
0.8011	Intermediate Similarity	NPC477552
0.8011	Intermediate Similarity	NPC477550
0.8	Intermediate Similarity	NPC471527
0.8	Intermediate Similarity	NPC475544
0.8	Intermediate Similarity	NPC315542
0.7989	Intermediate Similarity	NPC328763
0.7989	Intermediate Similarity	NPC470903
0.7989	Intermediate Similarity	NPC470112
0.7989	Intermediate Similarity	NPC167763
0.7988	Intermediate Similarity	NPC276506
0.7988	Intermediate Similarity	NPC196091
0.7976	Intermediate Similarity	NPC328649
0.7976	Intermediate Similarity	NPC141957
0.7975	Intermediate Similarity	NPC476268
0.7966	Intermediate Similarity	NPC234069
0.7963	Intermediate Similarity	NPC56685
0.7953	Intermediate Similarity	NPC136797
0.7944	Intermediate Similarity	NPC477638
0.7944	Intermediate Similarity	NPC477632
0.7941	Intermediate Similarity	NPC328494
0.7935	Intermediate Similarity	NPC127741
0.7935	Intermediate Similarity	NPC6570
0.7929	Intermediate Similarity	NPC186617
0.7923	Intermediate Similarity	NPC473450
0.791	Intermediate Similarity	NPC94862
0.7908	Intermediate Similarity	NPC257390
0.7898	Intermediate Similarity	NPC299806
0.7889	Intermediate Similarity	NPC314083
0.7882	Intermediate Similarity	NPC473693
0.7882	Intermediate Similarity	NPC471568
0.7866	Intermediate Similarity	NPC473580
0.7853	Intermediate Similarity	NPC122590
0.7844	Intermediate Similarity	NPC241794
0.7814	Intermediate Similarity	NPC323662
0.7778	Intermediate Similarity	NPC477526
0.7766	Intermediate Similarity	NPC220060
0.7765	Intermediate Similarity	NPC473502
0.7736	Intermediate Similarity	NPC161069
0.7725	Intermediate Similarity	NPC1390
0.7725	Intermediate Similarity	NPC287757
0.7725	Intermediate Similarity	NPC469444
0.7725	Intermediate Similarity	NPC319320
0.7725	Intermediate Similarity	NPC62104
0.7719	Intermediate Similarity	NPC280022
0.7717	Intermediate Similarity	NPC50548
0.7712	Intermediate Similarity	NPC469666
0.7702	Intermediate Similarity	NPC314358
0.7697	Intermediate Similarity	NPC138083
0.7688	Intermediate Similarity	NPC475532
0.7677	Intermediate Similarity	NPC326966
0.767	Intermediate Similarity	NPC32064
0.767	Intermediate Similarity	NPC153554
0.7669	Intermediate Similarity	NPC2501
0.7665	Intermediate Similarity	NPC326349
0.7665	Intermediate Similarity	NPC323336
0.7663	Intermediate Similarity	NPC144314
0.7661	Intermediate Similarity	NPC209463
0.7658	Intermediate Similarity	NPC313694
0.7658	Intermediate Similarity	NPC242159
0.7654	Intermediate Similarity	NPC276120
0.765	Intermediate Similarity	NPC59827
0.765	Intermediate Similarity	NPC184933
0.7644	Intermediate Similarity	NPC164608
0.7644	Intermediate Similarity	NPC165285
0.7644	Intermediate Similarity	NPC17698
0.764	Intermediate Similarity	NPC313867
0.764	Intermediate Similarity	NPC316008
0.764	Intermediate Similarity	NPC209509
0.7637	Intermediate Similarity	NPC477631
0.7634	Intermediate Similarity	NPC242728
0.7628	Intermediate Similarity	NPC244866
0.7614	Intermediate Similarity	NPC97526
0.7614	Intermediate Similarity	NPC119652
0.7611	Intermediate Similarity	NPC4910
0.7609	Intermediate Similarity	NPC149962
0.7604	Intermediate Similarity	NPC469445
0.7588	Intermediate Similarity	NPC289776
0.7588	Intermediate Similarity	NPC191863
0.7588	Intermediate Similarity	NPC133470
0.7579	Intermediate Similarity	NPC219350
0.7579	Intermediate Similarity	NPC194699
0.7578	Intermediate Similarity	NPC315283
0.7578	Intermediate Similarity	NPC476978
0.7578	Intermediate Similarity	NPC52748
0.7578	Intermediate Similarity	NPC314388
0.756	Intermediate Similarity	NPC56635
0.7546	Intermediate Similarity	NPC138775
0.7546	Intermediate Similarity	NPC135121
0.7544	Intermediate Similarity	NPC5719
0.7544	Intermediate Similarity	NPC22883
0.7544	Intermediate Similarity	NPC210377
0.7544	Intermediate Similarity	NPC217804
0.7531	Intermediate Similarity	NPC201244
0.7531	Intermediate Similarity	NPC5620
0.7531	Intermediate Similarity	NPC477217
0.7527	Intermediate Similarity	NPC477527
0.7527	Intermediate Similarity	NPC477636
0.7527	Intermediate Similarity	NPC29531
0.7515	Intermediate Similarity	NPC7817
0.7515	Intermediate Similarity	NPC475168
0.7514	Intermediate Similarity	NPC329731
0.7514	Intermediate Similarity	NPC129486
0.7514	Intermediate Similarity	NPC477639
0.75	Intermediate Similarity	NPC471821
0.75	Intermediate Similarity	NPC471820
0.7487	Intermediate Similarity	NPC123859
0.7485	Intermediate Similarity	NPC262077
0.7485	Intermediate Similarity	NPC470902
0.7484	Intermediate Similarity	NPC296712
0.7484	Intermediate Similarity	NPC471264
0.7484	Intermediate Similarity	NPC471265
0.7484	Intermediate Similarity	NPC68865
0.747	Intermediate Similarity	NPC162104
0.7459	Intermediate Similarity	NPC471563
0.7457	Intermediate Similarity	NPC63040

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 NPC294516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	400
0.2-0.3	771
0.3-0.4	1816
0.4-0.5	2965
0.5-0.6	2385
0.6-0.7	662
0.7-0.8	31
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
0.8098	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD8303	Discontinued
0.7778	Intermediate Similarity	NPD7608	Discontinued
0.7744	Intermediate Similarity	NPD7131	Phase 3
0.7676	Intermediate Similarity	NPD7811	Phase 3
0.7676	Intermediate Similarity	NPD7810	Phase 3
0.7619	Intermediate Similarity	NPD8019	Approved
0.7616	Intermediate Similarity	NPD7484	Phase 3
0.7616	Intermediate Similarity	NPD7485	Phase 3
0.7613	Intermediate Similarity	NPD3136	Phase 2
0.7546	Intermediate Similarity	NPD8323	Discontinued
0.7516	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7978	Discontinued
0.7515	Intermediate Similarity	NPD7495	Discontinued
0.7451	Intermediate Similarity	NPD4659	Approved
0.7442	Intermediate Similarity	NPD8031	Discontinued
0.7403	Intermediate Similarity	NPD3125	Approved
0.7375	Intermediate Similarity	NPD8173	Phase 2
0.7375	Intermediate Similarity	NPD8172	Phase 2
0.7365	Intermediate Similarity	NPD7303	Discontinued
0.7358	Intermediate Similarity	NPD6346	Approved
0.7346	Intermediate Similarity	NPD7450	Phase 2
0.7317	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6851	Approved
0.7308	Intermediate Similarity	NPD6853	Approved
0.7256	Intermediate Similarity	NPD6681	Discovery
0.7244	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4103	Phase 2
0.7213	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5745	Approved
0.7178	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD3400	Discontinued
0.7152	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2098	Approved
0.7125	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1330	Phase 2
0.7118	Intermediate Similarity	NPD7523	Phase 3
0.7088	Intermediate Similarity	NPD6297	Approved
0.7079	Intermediate Similarity	NPD4652	Approved
0.7078	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD8315	Phase 1
0.7063	Intermediate Similarity	NPD5746	Approved
0.7059	Intermediate Similarity	NPD7613	Discontinued
0.7039	Intermediate Similarity	NPD5137	Approved
0.7029	Intermediate Similarity	NPD2097	Approved
0.7022	Intermediate Similarity	NPD2888	Approved
0.7022	Intermediate Similarity	NPD2017	Approved
0.7022	Intermediate Similarity	NPD2890	Approved
0.7022	Intermediate Similarity	NPD2889	Approved
0.7006	Intermediate Similarity	NPD8245	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8417	Discontinued
0.6982	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2584	Suspended
0.6943	Remote Similarity	NPD2561	Approved
0.6943	Remote Similarity	NPD2562	Approved
0.6933	Remote Similarity	NPD8265	Approved
0.6928	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8025	Phase 2
0.6909	Remote Similarity	NPD3554	Approved
0.6909	Remote Similarity	NPD3552	Approved
0.6909	Remote Similarity	NPD3555	Approved
0.6909	Remote Similarity	NPD3553	Approved
0.6905	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8356	Approved
0.6882	Remote Similarity	NPD6666	Approved
0.6882	Remote Similarity	NPD6667	Approved
0.6875	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7451	Discontinued
0.6875	Remote Similarity	NPD7972	Discontinued
0.6867	Remote Similarity	NPD1753	Discontinued
0.6865	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6390	Discontinued
0.6848	Remote Similarity	NPD2568	Approved
0.6848	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6073	Approved
0.6842	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD5967	Approved
0.6824	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6294	Approved
0.6807	Remote Similarity	NPD6295	Approved
0.6802	Remote Similarity	NPD3536	Discontinued
0.6798	Remote Similarity	NPD8351	Phase 2
0.6791	Remote Similarity	NPD7280	Phase 3
0.6791	Remote Similarity	NPD7281	Phase 3
0.679	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5201	Approved
0.679	Remote Similarity	NPD4620	Approved
0.679	Remote Similarity	NPD5203	Approved
0.679	Remote Similarity	NPD4617	Approved
0.6788	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8076	Discontinued
0.678	Remote Similarity	NPD5773	Approved
0.678	Remote Similarity	NPD5772	Approved
0.678	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6405	Approved
0.6768	Remote Similarity	NPD6407	Approved
0.6765	Remote Similarity	NPD5481	Discontinued
0.6765	Remote Similarity	NPD6676	Phase 2
0.6765	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4731	Phase 3
0.6762	Remote Similarity	NPD8430	Approved
0.6761	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5485	Approved
0.6757	Remote Similarity	NPD5484	Approved
0.6748	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3052	Approved
0.6747	Remote Similarity	NPD3054	Approved
0.6736	Remote Similarity	NPD6312	Discontinued
0.6734	Remote Similarity	NPD8161	Suspended
0.6728	Remote Similarity	NPD4177	Approved
0.6728	Remote Similarity	NPD4175	Approved
0.6727	Remote Similarity	NPD5119	Approved
0.6727	Remote Similarity	NPD5120	Approved
0.6727	Remote Similarity	NPD5121	Approved
0.6727	Remote Similarity	NPD5296	Approved
0.6727	Remote Similarity	NPD8416	Discontinued
0.6726	Remote Similarity	NPD1725	Approved
0.6723	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6852	Discontinued
0.6703	Remote Similarity	NPD42	Phase 2
0.6703	Remote Similarity	NPD6042	Phase 2
0.6702	Remote Similarity	NPD7617	Discontinued
0.6687	Remote Similarity	NPD4677	Discontinued
0.6687	Remote Similarity	NPD8643	Discontinued
0.6686	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5218	Approved
0.6667	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5219	Approved
0.6667	Remote Similarity	NPD5557	Phase 1
0.6667	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7715	Approved
0.6649	Remote Similarity	NPD4435	Approved
0.6648	Remote Similarity	NPD7738	Approved
0.6648	Remote Similarity	NPD7737	Approved
0.6648	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5725	Approved
0.6647	Remote Similarity	NPD6088	Approved
0.6647	Remote Similarity	NPD5314	Approved
0.6646	Remote Similarity	NPD5723	Approved
0.6631	Remote Similarity	NPD5445	Approved
0.6631	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6862	Phase 2
0.663	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7011	Discontinued
0.6629	Remote Similarity	NPD5356	Approved
0.6629	Remote Similarity	NPD5355	Approved
0.6629	Remote Similarity	NPD1670	Discontinued
0.6628	Remote Similarity	NPD3692	Discontinued
0.6628	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6623	Phase 3
0.6625	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5304	Approved
0.6624	Remote Similarity	NPD5303	Approved
0.6617	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6256	Approved
0.6616	Remote Similarity	NPD6255	Approved
0.6616	Remote Similarity	NPD6254	Approved
0.6613	Remote Similarity	NPD5313	Approved
0.6613	Remote Similarity	NPD5312	Approved
0.6609	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4619	Approved
0.6606	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4621	Approved
0.6604	Remote Similarity	NPD3421	Phase 3
0.6603	Remote Similarity	NPD4574	Approved
0.6603	Remote Similarity	NPD4576	Approved
0.6603	Remote Similarity	NPD5292	Approved
0.6603	Remote Similarity	NPD3123	Discovery
0.6603	Remote Similarity	NPD5291	Approved
0.6599	Remote Similarity	NPD7565	Approved
0.6597	Remote Similarity	NPD4434	Approved
0.6596	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5823	Approved
0.6593	Remote Similarity	NPD2904	Discontinued
0.6591	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD555	Phase 2
0.658	Remote Similarity	NPD6504	Approved
0.658	Remote Similarity	NPD6505	Approved
0.6579	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7110	Phase 1
0.6573	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4186	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