NPASS Compound

Structure

CID50520 OpenBabel06191715382D 80 81 0 0 1 0 0 0 0 0999 V2000 -9.4467 3.1061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0094 9.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1787 10.3768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5050 9.9314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2399 7.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1001 -1.6297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5863 -2.1074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6067 -0.7949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9408 3.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0248 9.5147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6794 6.6953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5333 6.1749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8018 6.2159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4109 6.6543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9478 6.7362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2649 6.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3160 2.5863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0702 6.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9092 3.4999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1425 6.6134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5728 1.9172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8987 0.5670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8529 7.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4838 0.0276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4704 9.6709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2162 6.7772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7465 -0.6943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5482 -1.8339 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9409 3.9620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6838 8.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0741 1.1327 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0360 6.7793 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9147 3.3954 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7294 0.6841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8211 -0.4300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7618 8.3519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4295 0.3526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7276 8.7046 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3386 6.2978 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7923 -0.8642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7729 7.1224 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7801 -0.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8464 2.9664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5846 8.1404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4279 0.3695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5272 5.9082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9215 4.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7150 8.8627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0528 7.8163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3062 1.5009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8522 -0.5232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9965 6.0930 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -6.9189 -0.8613 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.5787 8.9287 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6208 1.3341 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6413 -0.2479 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.8330 4.9561 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7141 8.8188 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.5535 2.0103 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.3795 7.5336 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7922 8.3509 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7268 5.3762 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7817 -1.0089 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 1.7068 2.4172 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2659 -2.5302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6457 -0.9957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8538 8.7710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1838 -0.3039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5361 7.7686 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9382 -1.9390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8273 2.7718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1078 8.9926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1217 -0.3506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4434 6.3088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9170 4.4898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6577 9.8610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6702 8.6029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1773 1.0097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4179 -1.4240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 8 64 1 0 0 0 0 9 29 2 0 0 0 0 10 30 2 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 26 1 0 0 0 0 20 52 1 0 0 0 0 21 65 1 0 0 0 0 22 35 1 0 0 0 0 23 36 1 0 0 0 0 24 37 1 0 0 0 0 26 5 1 1 0 0 0 27 6 1 1 0 0 0 27 42 1 0 0 0 0 27 56 1 0 0 0 0 28 7 1 1 0 0 0 28 66 1 0 0 0 0 29 43 1 0 0 0 0 29 57 1 0 0 0 0 30 44 1 0 0 0 0 30 58 1 0 0 0 0 31 22 1 6 0 0 0 31 45 1 0 0 0 0 31 59 1 0 0 0 0 32 23 1 6 0 0 0 32 46 1 0 0 0 0 32 60 1 0 0 0 0 33 19 1 6 0 0 0 33 47 1 0 0 0 0 33 65 1 0 0 0 0 34 24 1 6 0 0 0 34 50 1 0 0 0 0 34 64 1 0 0 0 0 35 53 2 0 0 0 0 35 67 1 0 0 0 0 36 54 2 0 0 0 0 36 68 1 0 0 0 0 37 55 2 0 0 0 0 37 69 1 0 0 0 0 38 25 1 6 0 0 0 38 48 1 0 0 0 0 38 61 1 0 0 0 0 39 26 1 1 0 0 0 39 41 1 0 0 0 0 39 62 1 0 0 0 0 40 28 1 6 0 0 0 40 51 1 0 0 0 0 40 63 1 0 0 0 0 41 49 1 0 0 0 0 41 70 1 6 0 0 0 42 63 2 3 0 0 0 42 71 1 0 0 0 0 43 59 2 3 0 0 0 43 72 1 0 0 0 0 44 60 2 3 0 0 0 44 73 1 0 0 0 0 45 56 2 3 0 0 0 45 74 1 0 0 0 0 46 57 2 3 0 0 0 46 75 1 0 0 0 0 47 62 2 3 0 0 0 47 76 1 0 0 0 0 48 58 2 3 0 0 0 48 77 1 0 0 0 0 49 61 2 3 0 0 0 49 78 1 0 0 0 0 50 65 1 0 0 0 0 50 79 2 0 0 0 0 51 64 1 0 0 0 0 51 80 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1151.57
Volume:	1124.014
LogP:	0.286
LogD:	0.556
LogS:	-0.133
# Rotatable Bonds:	17
TPSA:	466.07
# H-Bond Aceptor:	28
# H-Bond Donor:	16
# Rings:	2
# Heavy Atoms:	29

MedChem Properties

QED Drug-Likeness Score:	0.033
Synthetic Accessibility Score:	7.578
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-3.347
MDCK Permeability:	0.0008777952753007412
Pgp-inhibitor:	0.668
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.428
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	32.729759216308594%
Volume Distribution (VD):	0.443
Pgp-substrate:	25.022966384887695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	1.654
Half-life (T1/2):	0.653

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.995
AMES Toxicity:	0.81
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.884
Carcinogencity:	0.289
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC50520

Natural Product ID:	NPC50520
*Common Name:**	Minutissamide B
IUPAC Name:	2-[(3S,6S,9R,12S,15E,18S,21E,24S,27R,28R,31S)-3,18-bis(2-amino-2-oxoethyl)-28-[(2S)-10-chlorodecan-2-yl]-15,21-di(ethylidene)-27-hydroxy-6-[(1R)-1-hydroxyethyl]-4,9-dimethyl-2,5,8,11,14,17,20,23,26,30-decaoxo-24-propan-2-yl-1,4,7,10,13,16,19,22,25,29-decazabicyclo[29.3.0]tetratriacontan-12-yl]acetamide
Synonyms:	Minutissamide B
Standard InCHIKey:	BVPWTFZHTABZAH-IXKBYUEASA-N
Standard InCHI:	InChI=1S/C51H82ClN13O15/c1-9-29-43(72)59-31(22-35(53)67)45(74)56-27(6)42(71)63-40(28(7)66)51(80)64(8)34(24-37(55)69)50(79)65-21-17-19-33(65)47(76)62-39(26(5)18-15-13-11-12-14-16-20-52)41(70)49(78)61-38(25(3)4)48(77)58-30(10-2)44(73)60-32(23-36(54)68)46(75)57-29/h9-10,25-28,31-34,38-41,66,70H,11-24H2,1-8H3,(H2,53,67)(H2,54,68)(H2,55,69)(H,56,74)(H,57,75)(H,58,77)(H,59,72)(H,60,73)(H,61,78)(H,62,76)(H,63,71)/b29-9+,30-10+/t26-,27+,28+,31-,32-,33-,34-,38-,39+,40-,41+/m0/s1
SMILES:	C/C=C/1C(=N[C@@H](CC(=N)O)C(=N[C@H](C)C(=N[C@@H]([C@@H](C)O)C(=O)N(C)[C@@H](CC(=N)O)C(=O)N2CCC[C@H]2C(=N[C@H]([C@@H](C)CCCCCCCCCl)[C@H](C(=N[C@@H](C(C)C)C(=N/C(=C/C)/C(=N[C@@H](CC(=N)O)C(=N1)O)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1814282
PubChem CID:	53467209
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
NPO28834	Anabaena minutissima	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21699148]
NPO28834	Anabaena minutissima	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	20000.0	nM	PMID[520799]

☑ 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 NPC50520 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	100
0.1-0.2	1749
0.2-0.3	22520
0.3-0.4	15481
0.4-0.5	2235
0.5-0.6	503
0.6-0.7	90
0.7-0.8	9
0.8-0.85	0
0.85-0.9	5
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9492	High Similarity	NPC470655
0.9492	High Similarity	NPC470651
0.9381	High Similarity	NPC296043
0.9298	High Similarity	NPC329216
0.8983	High Similarity	NPC160688
0.8898	High Similarity	NPC470652
0.8607	High Similarity	NPC470654
0.8607	High Similarity	NPC470653
0.8607	High Similarity	NPC470650
0.7333	Intermediate Similarity	NPC476877
0.7213	Intermediate Similarity	NPC476876
0.7099	Intermediate Similarity	NPC315188
0.6975	Remote Similarity	NPC47076
0.6975	Remote Similarity	NPC134504
0.6935	Remote Similarity	NPC241394
0.6929	Remote Similarity	NPC476875
0.6855	Remote Similarity	NPC128303
0.6833	Remote Similarity	NPC473597
0.6667	Remote Similarity	NPC475637
0.6562	Remote Similarity	NPC207820
0.6444	Remote Similarity	NPC469899
0.6387	Remote Similarity	NPC275715
0.6324	Remote Similarity	NPC477237
0.632	Remote Similarity	NPC220234
0.6316	Remote Similarity	NPC476243
0.6316	Remote Similarity	NPC476156
0.6316	Remote Similarity	NPC476137
0.6316	Remote Similarity	NPC476117
0.6308	Remote Similarity	NPC171734
0.6306	Remote Similarity	NPC316244
0.6261	Remote Similarity	NPC476302
0.6232	Remote Similarity	NPC477238
0.6228	Remote Similarity	NPC31756
0.6214	Remote Similarity	NPC36254
0.6205	Remote Similarity	NPC477462
0.6187	Remote Similarity	NPC273185
0.6183	Remote Similarity	NPC67009
0.6148	Remote Similarity	NPC472536
0.6148	Remote Similarity	NPC103391
0.6094	Remote Similarity	NPC188785
0.609	Remote Similarity	NPC7817
0.609	Remote Similarity	NPC251122
0.609	Remote Similarity	NPC475168
0.608	Remote Similarity	NPC469739
0.6074	Remote Similarity	NPC471202
0.6074	Remote Similarity	NPC63191
0.6068	Remote Similarity	NPC184473
0.6051	Remote Similarity	NPC315809
0.6051	Remote Similarity	NPC314050
0.6047	Remote Similarity	NPC301148
0.6047	Remote Similarity	NPC5864
0.6047	Remote Similarity	NPC124554
0.6047	Remote Similarity	NPC314387
0.6026	Remote Similarity	NPC2501
0.6014	Remote Similarity	NPC287401
0.6014	Remote Similarity	NPC477400
0.6	Remote Similarity	NPC477539
0.5984	Remote Similarity	NPC322966
0.5983	Remote Similarity	NPC470783
0.5975	Remote Similarity	NPC470902
0.5968	Remote Similarity	NPC471098
0.5968	Remote Similarity	NPC315237
0.5968	Remote Similarity	NPC62263
0.5968	Remote Similarity	NPC173763
0.5963	Remote Similarity	NPC197743
0.5963	Remote Similarity	NPC297145
0.5959	Remote Similarity	NPC120335
0.5954	Remote Similarity	NPC124549
0.5944	Remote Similarity	NPC309525
0.5938	Remote Similarity	NPC475440
0.5932	Remote Similarity	NPC53858
0.5932	Remote Similarity	NPC84128
0.5923	Remote Similarity	NPC475149
0.5923	Remote Similarity	NPC471097
0.5921	Remote Similarity	NPC477401
0.5921	Remote Similarity	NPC477399
0.5912	Remote Similarity	NPC122590
0.5903	Remote Similarity	NPC473249
0.5893	Remote Similarity	NPC328494
0.5891	Remote Similarity	NPC475791
0.5891	Remote Similarity	NPC13175
0.5887	Remote Similarity	NPC474576
0.5882	Remote Similarity	NPC469427
0.5882	Remote Similarity	NPC469426
0.5878	Remote Similarity	NPC198344
0.5833	Remote Similarity	NPC472351
0.5833	Remote Similarity	NPC314358
0.5833	Remote Similarity	NPC323720
0.5817	Remote Similarity	NPC476259
0.5814	Remote Similarity	NPC475758
0.5808	Remote Similarity	NPC209463
0.5806	Remote Similarity	NPC475801
0.5806	Remote Similarity	NPC52748
0.5806	Remote Similarity	NPC474593
0.5798	Remote Similarity	NPC284456
0.5798	Remote Similarity	NPC6902
0.5782	Remote Similarity	NPC319766
0.5779	Remote Similarity	NPC71866
0.5779	Remote Similarity	NPC309450
0.5779	Remote Similarity	NPC304299
0.5779	Remote Similarity	NPC475266
0.5779	Remote Similarity	NPC247776
0.5779	Remote Similarity	NPC475278
0.5778	Remote Similarity	NPC133729
0.5769	Remote Similarity	NPC315266
0.5769	Remote Similarity	NPC233932
0.5769	Remote Similarity	NPC313867
0.5769	Remote Similarity	NPC316008
0.575	Remote Similarity	NPC477730
0.5741	Remote Similarity	NPC244509
0.5738	Remote Similarity	NPC323662
0.5732	Remote Similarity	NPC469898
0.5726	Remote Similarity	NPC155230
0.5705	Remote Similarity	NPC315283
0.5705	Remote Similarity	NPC314388
0.5694	Remote Similarity	NPC16709
0.569	Remote Similarity	NPC470782
0.568	Remote Similarity	NPC477729
0.5678	Remote Similarity	NPC312315
0.5676	Remote Similarity	NPC313657
0.5652	Remote Similarity	NPC478024
0.5652	Remote Similarity	NPC162104
0.5652	Remote Similarity	NPC314550
0.5649	Remote Similarity	NPC315848
0.5649	Remote Similarity	NPC315210
0.5641	Remote Similarity	NPC176226
0.564	Remote Similarity	NPC471165
0.5636	Remote Similarity	NPC244336
0.5635	Remote Similarity	NPC477538
0.5616	Remote Similarity	NPC46427
0.5608	Remote Similarity	NPC313962
0.5604	Remote Similarity	NPC328763
0.5602	Remote Similarity	NPC114806

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 NPC50520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	78
0.1-0.2	474
0.2-0.3	4055
0.3-0.4	3885
0.4-0.5	583
0.5-0.6	70
0.6-0.7	5
0.7-0.8	0
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
0.6696	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.624	Remote Similarity	NPD8038	Phase 2
0.6148	Remote Similarity	NPD7915	Approved
0.6148	Remote Similarity	NPD7916	Approved
0.6134	Remote Similarity	NPD7760	Phase 2
0.6134	Remote Similarity	NPD7759	Phase 2
0.6047	Remote Similarity	NPD3182	Approved
0.6047	Remote Similarity	NPD3185	Approved
0.6047	Remote Similarity	NPD3183	Approved
0.6047	Remote Similarity	NPD3184	Approved
0.6033	Remote Similarity	NPD3177	Phase 3
0.6016	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD4261	Phase 1
0.6	Remote Similarity	NPD6122	Discontinued
0.5932	Remote Similarity	NPD2683	Discontinued
0.5903	Remote Similarity	NPD7747	Phase 1
0.5903	Remote Similarity	NPD7746	Phase 1
0.5852	Remote Similarity	NPD3188	Approved
0.5789	Remote Similarity	NPD8173	Phase 2
0.5789	Remote Similarity	NPD8172	Phase 2
0.5714	Remote Similarity	NPD7763	Phase 2
0.5714	Remote Similarity	NPD7762	Phase 2
0.5616	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5613	Remote Similarity	NPD8384	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