NPASS Compound

Structure

NPC128303 OpenBabel07101718232D 71 72 0 0 1 0 0 0 0 0999 V2000 -6.2290 0.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9506 -3.6731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2280 -3.4920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4279 -8.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7234 -7.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3848 -2.5868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6803 -4.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3330 -9.0161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3275 -8.9115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1542 -5.0424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5610 -4.1289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5380 -0.5043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8689 -1.2475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8907 -1.0396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2216 -1.7827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2435 -1.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1849 -7.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2894 -8.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9325 -5.0743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7054 -8.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2828 0.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2099 -4.8933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8815 1.1061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0370 -4.0798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6189 -8.0579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5758 -3.1745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0189 -5.4811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8761 1.2106 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2713 -7.3337 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8963 -7.8768 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5396 -0.3720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2030 -9.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6622 -2.7678 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0009 -6.8823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4623 -7.9215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6442 -1.3666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8532 -3.3556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2533 -5.9324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8262 -7.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7398 -8.1025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1487 -4.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3145 -3.8987 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3075 -10.1362 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9144 -6.4756 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1668 -6.3392 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0172 -8.2836 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5577 -1.7733 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5488 -7.5147 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9578 -4.3501 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6736 0.1280 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3761 2.0767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0120 -8.5539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1919 -6.2945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5669 -8.9160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8352 -1.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9397 -2.9489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6555 -1.2733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4443 -6.5202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7217 -6.7013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 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 6 31 1 0 0 0 0 7 31 1 0 0 0 0 8 49 1 0 0 0 0 9 49 1 0 0 0 0 10 50 1 0 0 0 0 11 50 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 40 1 0 0 0 0 20 21 1 0 0 0 0 21 39 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 33 1 0 0 0 0 24 37 1 0 0 0 0 25 34 1 0 0 0 0 25 38 1 0 0 0 0 26 32 1 0 0 0 0 26 51 1 0 0 0 0 27 34 1 0 0 0 0 27 59 1 0 0 0 0 28 33 1 0 0 0 0 28 60 1 0 0 0 0 32 22 1 1 0 0 0 32 53 1 0 0 0 0 33 61 1 6 0 0 0 34 62 1 6 0 0 0 35 20 1 1 0 0 0 35 43 1 0 0 0 0 35 54 1 0 0 0 0 36 23 1 1 0 0 0 36 42 1 0 0 0 0 36 55 1 0 0 0 0 37 44 1 1 0 0 0 37 60 1 0 0 0 0 38 46 1 1 0 0 0 38 59 1 0 0 0 0 39 52 2 0 0 0 0 39 63 1 0 0 0 0 40 59 1 0 0 0 0 40 64 2 0 0 0 0 41 31 1 1 0 0 0 41 45 1 0 0 0 0 41 56 1 0 0 0 0 42 53 2 3 0 0 0 42 65 1 0 0 0 0 43 57 2 3 0 0 0 43 66 1 0 0 0 0 44 56 2 3 0 0 0 44 67 1 0 0 0 0 45 58 2 3 0 0 0 45 68 1 0 0 0 0 46 60 1 0 0 0 0 46 69 2 0 0 0 0 47 50 1 0 0 0 0 47 54 2 3 0 0 0 47 70 1 0 0 0 0 48 49 1 0 0 0 0 48 55 2 3 0 0 0 48 71 1 0 0 0 0 49 57 1 0 0 0 0 50 58 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1006.68
Volume:	1039.175
LogP:	1.893
LogD:	2.188
LogS:	-2.637
# Rotatable Bonds:	36
TPSA:	332.76
# H-Bond Aceptor:	21
# H-Bond Donor:	12
# Rings:	2
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.028
Synthetic Accessibility Score:	5.882
Fsp3:	0.82
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.002
MDCK Permeability:	0.0002627709473017603
Pgp-inhibitor:	0.671
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.933
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	53.08495330810547%
Volume Distribution (VD):	0.742
Pgp-substrate:	39.60797882080078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.533
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	1.007
Half-life (T1/2):	0.715

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.711
Carcinogencity:	0.394
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC128303

Natural Product ID:	NPC128303
*Common Name:**	Cicadapeptin I
IUPAC Name:	(2S)-N-[1-[[(2S)-1-[[(2S)-1-amino-4-methylpentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]-2-[[2-[[(2S)-2-[[(2S,4R)-1-[(2S,4R)-1-decanoyl-4-hydroxypyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]pentanediamide
Synonyms:	Cicadapeptin I
Standard InCHIKey:	NVJOHXLMVTYSFU-DSBHZGLUSA-N
Standard InCHI:	InChI=1S/C50H90N10O11/c1-12-13-14-15-16-17-18-19-40(64)59-27-34(62)25-38(59)46(69)60-28-33(61)24-37(60)44(67)56-41(31(6)7)45(68)58-50(10,11)47(70)54-35(20-21-39(52)63)43(66)57-49(8,9)48(71)55-36(23-30(4)5)42(65)53-32(26-51)22-29(2)3/h29-38,41,61-62H,12-28,51H2,1-11H3,(H2,52,63)(H,53,65)(H,54,70)(H,55,71)(H,56,67)(H,57,66)(H,58,68)/t32-,33+,34+,35-,36-,37-,38-,41-/m0/s1
SMILES:	CCCCCCCCCC(=O)N1C[C@@H](C[C@H]1C(=O)N1C[C@@H](C[C@H]1C(=N[C@H](C(=NC(C(=N[C@H](C(=NC(C(=N[C@H](C(=N[C@@H](CC(C)C)CN)O)CC(C)C)O)(C)C)O)CCC(=N)O)O)(C)C)O)C(C)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448005
PubChem CID:	11400450
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO33185	cordyceps heteropoda	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679316]

☑ 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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	=	13.0	mm	PMID[548392]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	13.0	mm	PMID[548392]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	16.0	mm	PMID[548392]

☑ 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 NPC128303 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	251
0.1-0.2	12101
0.2-0.3	20286
0.3-0.4	7965
0.4-0.5	1445
0.5-0.6	481
0.6-0.7	121
0.7-0.8	37
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC241394
0.78	Intermediate Similarity	NPC275715
0.7788	Intermediate Similarity	NPC134504
0.7788	Intermediate Similarity	NPC47076
0.7677	Intermediate Similarity	NPC477539
0.75	Intermediate Similarity	NPC31756
0.7423	Intermediate Similarity	NPC476137
0.7423	Intermediate Similarity	NPC476156
0.7423	Intermediate Similarity	NPC476117
0.7423	Intermediate Similarity	NPC476243
0.7395	Intermediate Similarity	NPC160688
0.7373	Intermediate Similarity	NPC469899
0.7347	Intermediate Similarity	NPC476302
0.7265	Intermediate Similarity	NPC296043
0.7241	Intermediate Similarity	NPC471202
0.7241	Intermediate Similarity	NPC63191
0.7213	Intermediate Similarity	NPC470654
0.7213	Intermediate Similarity	NPC470653
0.7213	Intermediate Similarity	NPC470650
0.7203	Intermediate Similarity	NPC329216
0.7172	Intermediate Similarity	NPC470783
0.7143	Intermediate Similarity	NPC323720
0.7143	Intermediate Similarity	NPC477538
0.71	Intermediate Similarity	NPC84128
0.71	Intermediate Similarity	NPC53858
0.7054	Intermediate Similarity	NPC476877
0.7025	Intermediate Similarity	NPC470652
0.7	Intermediate Similarity	NPC475440
0.7	Intermediate Similarity	NPC220234
0.6981	Remote Similarity	NPC474576
0.697	Remote Similarity	NPC312315
0.6961	Remote Similarity	NPC472351
0.6957	Remote Similarity	NPC207820
0.6942	Remote Similarity	NPC477237
0.693	Remote Similarity	NPC476876
0.6916	Remote Similarity	NPC173763
0.6916	Remote Similarity	NPC471098
0.6916	Remote Similarity	NPC62263
0.6887	Remote Similarity	NPC475801
0.6887	Remote Similarity	NPC474593
0.6855	Remote Similarity	NPC50520
0.6832	Remote Similarity	NPC23984
0.6829	Remote Similarity	NPC477238
0.6818	Remote Similarity	NPC473597
0.6699	Remote Similarity	NPC235078
0.6667	Remote Similarity	NPC5864
0.6667	Remote Similarity	NPC301148
0.6667	Remote Similarity	NPC124554
0.6641	Remote Similarity	NPC470655
0.6641	Remote Similarity	NPC470651
0.6639	Remote Similarity	NPC476875
0.6638	Remote Similarity	NPC475637
0.6636	Remote Similarity	NPC322966
0.6609	Remote Similarity	NPC198344
0.6566	Remote Similarity	NPC327272
0.656	Remote Similarity	NPC315188
0.6552	Remote Similarity	NPC124549
0.6525	Remote Similarity	NPC67009
0.6505	Remote Similarity	NPC475542
0.6465	Remote Similarity	NPC256312
0.6465	Remote Similarity	NPC266888
0.6465	Remote Similarity	NPC161774
0.6465	Remote Similarity	NPC126186
0.6396	Remote Similarity	NPC301010
0.6387	Remote Similarity	NPC171734
0.6364	Remote Similarity	NPC29326
0.6364	Remote Similarity	NPC476019
0.6357	Remote Similarity	NPC309525
0.6339	Remote Similarity	NPC280066
0.6337	Remote Similarity	NPC470782
0.63	Remote Similarity	NPC209156
0.63	Remote Similarity	NPC320221
0.629	Remote Similarity	NPC271115
0.6273	Remote Similarity	NPC477729
0.6263	Remote Similarity	NPC196007
0.6263	Remote Similarity	NPC214532
0.6263	Remote Similarity	NPC76297
0.625	Remote Similarity	NPC141050
0.625	Remote Similarity	NPC296143
0.6239	Remote Similarity	NPC471097
0.6239	Remote Similarity	NPC475149
0.6214	Remote Similarity	NPC77905
0.6207	Remote Similarity	NPC475791
0.6207	Remote Similarity	NPC13175
0.6161	Remote Similarity	NPC315237
0.6133	Remote Similarity	NPC469901
0.6129	Remote Similarity	NPC309731
0.6121	Remote Similarity	NPC475758
0.6119	Remote Similarity	NPC120335
0.6111	Remote Similarity	NPC28542
0.6061	Remote Similarity	NPC322274
0.6058	Remote Similarity	NPC477400
0.6056	Remote Similarity	NPC52748
0.604	Remote Similarity	NPC316244
0.6038	Remote Similarity	NPC314466
0.6019	Remote Similarity	NPC155670
0.6019	Remote Similarity	NPC145748
0.6019	Remote Similarity	NPC95478
0.6014	Remote Similarity	NPC315266
0.6	Remote Similarity	NPC117829
0.5984	Remote Similarity	NPC15413
0.5963	Remote Similarity	NPC227051
0.5962	Remote Similarity	NPC59867
0.596	Remote Similarity	NPC250953
0.596	Remote Similarity	NPC469898
0.5959	Remote Similarity	NPC2501
0.5957	Remote Similarity	NPC477401
0.5957	Remote Similarity	NPC477399
0.5942	Remote Similarity	NPC287401
0.5941	Remote Similarity	NPC470781
0.5926	Remote Similarity	NPC313657
0.5912	Remote Similarity	NPC469900
0.5912	Remote Similarity	NPC130309
0.5909	Remote Similarity	NPC477518
0.5906	Remote Similarity	NPC470621
0.5906	Remote Similarity	NPC222481
0.5905	Remote Similarity	NPC37681
0.5897	Remote Similarity	NPC473000
0.589	Remote Similarity	NPC471820
0.589	Remote Similarity	NPC471821
0.5882	Remote Similarity	NPC188785
0.5878	Remote Similarity	NPC273185
0.5859	Remote Similarity	NPC209734
0.5852	Remote Similarity	NPC25327
0.5852	Remote Similarity	NPC8325
0.5849	Remote Similarity	NPC315535
0.5849	Remote Similarity	NPC315131
0.5849	Remote Similarity	NPC478017
0.5839	Remote Similarity	NPC122590
0.5833	Remote Similarity	NPC476978
0.5827	Remote Similarity	NPC259586
0.5804	Remote Similarity	NPC324506
0.5802	Remote Similarity	NPC266910
0.5789	Remote Similarity	NPC211848
0.5789	Remote Similarity	NPC297145
0.5789	Remote Similarity	NPC197743
0.5782	Remote Similarity	NPC240848
0.576	Remote Similarity	NPC251122
0.5758	Remote Similarity	NPC287693
0.5758	Remote Similarity	NPC128005
0.5758	Remote Similarity	NPC84182
0.5755	Remote Similarity	NPC191774
0.5755	Remote Similarity	NPC316242
0.5743	Remote Similarity	NPC472579
0.5726	Remote Similarity	NPC469739
0.5714	Remote Similarity	NPC475188
0.5703	Remote Similarity	NPC472536
0.5703	Remote Similarity	NPC103391
0.57	Remote Similarity	NPC78312
0.57	Remote Similarity	NPC221764
0.57	Remote Similarity	NPC135539
0.57	Remote Similarity	NPC196359
0.5691	Remote Similarity	NPC471844
0.5688	Remote Similarity	NPC246005
0.5688	Remote Similarity	NPC284456
0.5688	Remote Similarity	NPC184473
0.5688	Remote Similarity	NPC6902
0.5678	Remote Similarity	NPC471843
0.5678	Remote Similarity	NPC313821
0.567	Remote Similarity	NPC314510
0.5669	Remote Similarity	NPC314550
0.5664	Remote Similarity	NPC473495
0.5664	Remote Similarity	NPC52533
0.5658	Remote Similarity	NPC477398
0.5657	Remote Similarity	NPC41429
0.5657	Remote Similarity	NPC262615
0.5657	Remote Similarity	NPC160661
0.5656	Remote Similarity	NPC265094
0.5652	Remote Similarity	NPC477462
0.5646	Remote Similarity	NPC262077
0.5631	Remote Similarity	NPC306973
0.5614	Remote Similarity	NPC155230
0.5607	Remote Similarity	NPC477145
0.5607	Remote Similarity	NPC473741
0.5606	Remote Similarity	NPC139867

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 NPC128303 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	92
0.1-0.2	1630
0.2-0.3	5003
0.3-0.4	1866
0.4-0.5	439
0.5-0.6	96
0.6-0.7	15
0.7-0.8	7
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8776	High Similarity	NPD7841	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD8038	Phase 2
0.7879	Intermediate Similarity	NPD3177	Phase 3
0.7822	Intermediate Similarity	NPD4261	Phase 1
0.7708	Intermediate Similarity	NPD7762	Phase 2
0.7708	Intermediate Similarity	NPD7763	Phase 2
0.75	Intermediate Similarity	NPD7759	Phase 2
0.75	Intermediate Similarity	NPD7760	Phase 2
0.7157	Intermediate Similarity	NPD3723	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2683	Discontinued
0.6822	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1125	Discovery
0.6757	Remote Similarity	NPD3714	Approved
0.6757	Remote Similarity	NPD3715	Approved
0.6757	Remote Similarity	NPD3713	Approved
0.6754	Remote Similarity	NPD6122	Discontinued
0.6724	Remote Similarity	NPD6937	Approved
0.6667	Remote Similarity	NPD2682	Approved
0.6606	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6120	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4825	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD620	Approved
0.6216	Remote Similarity	NPD5792	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD3176	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7652	Discontinued
0.6107	Remote Similarity	NPD8041	Phase 2
0.6	Remote Similarity	NPD8298	Phase 2
0.5957	Remote Similarity	NPD6077	Discontinued
0.5909	Remote Similarity	NPD5791	Phase 2
0.5882	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD1439	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7915	Approved
0.5827	Remote Similarity	NPD7916	Approved
0.5818	Remote Similarity	NPD9401	Discovery
0.578	Remote Similarity	NPD4829	Discontinued
0.5776	Remote Similarity	NPD8394	Approved
0.5772	Remote Similarity	NPD8175	Discontinued
0.5755	Remote Similarity	NPD4278	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD4815	Discontinued
0.57	Remote Similarity	NPD8868	Approved
0.5686	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD1784	Approved
0.5678	Remote Similarity	NPD3189	Approved
0.5678	Remote Similarity	NPD3190	Approved
0.5678	Remote Similarity	NPD3191	Approved
0.5657	Remote Similarity	NPD6437	Approved
0.5657	Remote Similarity	NPD6438	Approved
0.5656	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD2132	Phase 3
0.5634	Remote Similarity	NPD5767	Discontinued
0.563	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD1689	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data