NPASS Compound

Structure

NPC470651 OpenBabel07101719172D 84 85 0 0 1 0 0 0 0 0999 V2000 -2.8203 -14.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4309 -6.4076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2110 -8.5935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5008 -8.8674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2599 -6.9647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9963 3.5632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8933 1.0048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8249 -2.7739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3216 2.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8776 0.4794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4235 4.0197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8285 -14.2199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4604 -6.6484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2884 -10.5283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8952 -9.7334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6735 -11.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5102 -8.8105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0667 -12.2461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9773 -3.7115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1169 -8.0156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4517 -13.1690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2342 -4.3806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4465 2.6947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9700 3.5740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5706 -2.7979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3443 -0.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2768 -8.2368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7319 -7.0927 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0537 2.5649 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7821 0.0110 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1659 -3.5261 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6684 2.3051 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4435 -13.2970 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.7665 -5.9283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9232 1.8425 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3681 -3.8806 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3881 -0.9216 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4933 4.4262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5687 0.3458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1187 -7.2493 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 -8.8658 -0.3896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1851 -3.3314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2858 1.5185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1908 -6.8210 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0663 2.4068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4128 -5.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0225 2.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0324 -4.7969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0851 -6.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3746 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2795 -2.3358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1309 -7.1620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5828 -1.9025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5657 0.8246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0503 -12.5021 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -7.0168 5.3054 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5248 0.6387 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0527 2.5210 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9799 -6.5457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.7181 1.2358 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1204 -7.3067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6092 -5.6138 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.8921 -4.2875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.1716 -1.3417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1309 2.0531 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 0.5761 -2.9024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.5871 -0.5823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4878 -4.4728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4929 4.3991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8369 1.0274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7565 -7.7218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8091 3.3731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2374 -5.7308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3634 3.2169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8386 -5.2881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4387 -7.9275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1915 1.0583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2795 -2.3291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8868 -8.1317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5783 -1.8080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1974 1.4708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0409 3.2331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 10 67 1 0 0 0 0 11 84 1 0 0 0 0 12 33 1 0 0 0 0 13 34 2 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 19 25 1 0 0 0 0 20 28 1 0 0 0 0 21 33 1 0 0 0 0 23 24 1 0 0 0 0 24 38 1 0 0 0 0 25 68 1 0 0 0 0 26 39 1 0 0 0 0 28 5 1 1 0 0 0 29 6 1 6 0 0 0 29 46 1 0 0 0 0 29 59 1 0 0 0 0 30 7 1 6 0 0 0 30 69 1 0 0 0 0 31 8 1 6 0 0 0 31 70 1 0 0 0 0 32 9 1 6 0 0 0 32 84 1 0 0 0 0 33 56 1 0 0 0 0 34 47 1 0 0 0 0 34 60 1 0 0 0 0 35 23 1 1 0 0 0 35 48 1 0 0 0 0 35 61 1 0 0 0 0 36 22 1 1 0 0 0 36 49 1 0 0 0 0 36 68 1 0 0 0 0 37 26 1 1 0 0 0 37 54 1 0 0 0 0 37 67 1 0 0 0 0 38 57 2 0 0 0 0 38 71 1 0 0 0 0 39 58 2 0 0 0 0 39 72 1 0 0 0 0 40 27 1 1 0 0 0 40 50 1 0 0 0 0 40 62 1 0 0 0 0 41 28 1 6 0 0 0 41 45 1 0 0 0 0 41 63 1 0 0 0 0 42 30 1 1 0 0 0 42 51 1 0 0 0 0 42 65 1 0 0 0 0 43 31 1 1 0 0 0 43 52 1 0 0 0 0 43 64 1 0 0 0 0 44 32 1 1 0 0 0 44 55 1 0 0 0 0 44 66 1 0 0 0 0 45 53 1 0 0 0 0 45 73 1 1 0 0 0 46 66 2 3 0 0 0 46 74 1 0 0 0 0 47 64 2 3 0 0 0 47 75 1 0 0 0 0 48 59 2 3 0 0 0 48 76 1 0 0 0 0 49 63 2 3 0 0 0 49 77 1 0 0 0 0 50 60 2 3 0 0 0 50 78 1 0 0 0 0 51 61 2 3 0 0 0 51 79 1 0 0 0 0 52 65 2 3 0 0 0 52 80 1 0 0 0 0 53 62 2 3 0 0 0 53 81 1 0 0 0 0 54 68 1 0 0 0 0 54 82 2 0 0 0 0 55 67 1 0 0 0 0 55 83 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1212.65
Volume:	1196.265
LogP:	1.079
LogD:	0.816
LogS:	-0.594
# Rotatable Bonds:	20
TPSA:	448.95
# H-Bond Aceptor:	28
# H-Bond Donor:	15
# Rings:	2
# Heavy Atoms:	29

MedChem Properties

QED Drug-Likeness Score:	0.027
Synthetic Accessibility Score:	7.794
Fsp3:	0.745
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:	-3.927
MDCK Permeability:	0.0007976144552230835
Pgp-inhibitor:	0.96
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.362
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.836
Plasma Protein Binding (PPB):	34.82225036621094%
Volume Distribution (VD):	0.442
Pgp-substrate:	33.366058349609375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.031
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	1.405
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.609
Carcinogencity:	0.195
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC470651

Natural Product ID:	NPC470651
*Common Name:**	Minutissamide F
IUPAC Name:	3-[(3S,6S,9R,12S,15S,18S,21E,24S,27R,28R,31S)-3-(2-amino-2-oxoethyl)-28-[(2S)-10-chlorododecan-2-yl]-21-ethylidene-27-hydroxy-15,18-bis[(1R)-1-hydroxyethyl]-6-[(1R)-1-methoxyethyl]-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]propanamide
Synonyms:	Minutissamide F
Standard InCHIKey:	QDBDOUAQHHPCNC-SOYRVYTOSA-N
Standard InCHI:	InChI=1S/C55H93ClN12O16/c1-12-33(56)21-18-16-14-15-17-20-28(5)41-45(73)53(81)62-40(27(3)4)50(78)60-34(13-2)47(75)64-43(31(8)70)52(80)65-42(30(7)69)51(79)61-35(23-24-38(57)71)48(76)59-29(6)46(74)66-44(32(9)84-11)55(83)67(10)37(26-39(58)72)54(82)68-25-19-22-36(68)49(77)63-41/h13,27-33,35-37,40-45,69-70,73H,12,14-26H2,1-11H3,(H2,57,71)(H2,58,72)(H,59,76)(H,60,78)(H,61,79)(H,62,81)(H,63,77)(H,64,75)(H,65,80)(H,66,74)/b34-13+/t28-,29+,30+,31+,32+,33?,35-,36-,37-,40-,41+,42-,43-,44-,45+/m0/s1
SMILES:	CCC(CCCCCCCC(C)C1C(C(=O)NC(C(=O)NC(=CC)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N2CCCC2C(=O)N1)CC(=O)N)C)C(C)OC)C)CCC(=O)N)C(C)O)C(C)O)C(C)C)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2148017
PubChem CID:	71461884
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO30928	Anabaena sp.	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16562836]
NPO30928	Anabaena sp.	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22980217]
NPO30928	Anabaena sp.	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[6806241]

☑ 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
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	1200.0	nM	PMID[483021]

☑ 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 NPC470651 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	104
0.1-0.2	1500
0.2-0.3	22037
0.3-0.4	16128
0.4-0.5	2293
0.5-0.6	502
0.6-0.7	116
0.7-0.8	7
0.8-0.85	0
0.85-0.9	3
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470655
0.9492	High Similarity	NPC50520
0.9402	High Similarity	NPC470652
0.9091	High Similarity	NPC470650
0.9091	High Similarity	NPC470654
0.9091	High Similarity	NPC470653
0.8983	High Similarity	NPC329216
0.8898	High Similarity	NPC296043
0.8689	High Similarity	NPC160688
0.7015	Intermediate Similarity	NPC315188
0.696	Remote Similarity	NPC476877
0.685	Remote Similarity	NPC476876
0.685	Remote Similarity	NPC475637
0.6748	Remote Similarity	NPC47076
0.6748	Remote Similarity	NPC473597
0.6748	Remote Similarity	NPC134504
0.6719	Remote Similarity	NPC241394
0.6718	Remote Similarity	NPC476875
0.6641	Remote Similarity	NPC128303
0.6618	Remote Similarity	NPC477237
0.6561	Remote Similarity	NPC316244
0.6522	Remote Similarity	NPC477238
0.6508	Remote Similarity	NPC220234
0.6489	Remote Similarity	NPC171734
0.6446	Remote Similarity	NPC477462
0.637	Remote Similarity	NPC63191
0.637	Remote Similarity	NPC471202
0.6364	Remote Similarity	NPC207820
0.6364	Remote Similarity	NPC67009
0.6357	Remote Similarity	NPC273185
0.6346	Remote Similarity	NPC7817
0.6346	Remote Similarity	NPC475168
0.6329	Remote Similarity	NPC470902
0.6324	Remote Similarity	NPC103391
0.6324	Remote Similarity	NPC472536
0.6282	Remote Similarity	NPC2501
0.6233	Remote Similarity	NPC120335
0.6231	Remote Similarity	NPC124554
0.6231	Remote Similarity	NPC301148
0.6231	Remote Similarity	NPC5864
0.6224	Remote Similarity	NPC309525
0.6203	Remote Similarity	NPC315809
0.6203	Remote Similarity	NPC314050
0.6186	Remote Similarity	NPC476302
0.6179	Remote Similarity	NPC275715
0.6164	Remote Similarity	NPC122590
0.6154	Remote Similarity	NPC188785
0.6154	Remote Similarity	NPC36254
0.6148	Remote Similarity	NPC251122
0.6143	Remote Similarity	NPC469899
0.6136	Remote Similarity	NPC124549
0.6111	Remote Similarity	NPC197743
0.6111	Remote Similarity	NPC297145
0.6107	Remote Similarity	NPC314387
0.6102	Remote Similarity	NPC476117
0.6102	Remote Similarity	NPC476243
0.6102	Remote Similarity	NPC476156
0.6102	Remote Similarity	NPC476137
0.6067	Remote Similarity	NPC477400
0.6061	Remote Similarity	NPC198344
0.6044	Remote Similarity	NPC323662
0.6032	Remote Similarity	NPC173763
0.6032	Remote Similarity	NPC315237
0.6032	Remote Similarity	NPC62263
0.6032	Remote Similarity	NPC471098
0.6017	Remote Similarity	NPC31756
0.6	Remote Similarity	NPC475440
0.6	Remote Similarity	NPC477729
0.5985	Remote Similarity	NPC471097
0.5985	Remote Similarity	NPC475149
0.5974	Remote Similarity	NPC477401
0.5974	Remote Similarity	NPC477399
0.5962	Remote Similarity	NPC52748
0.5954	Remote Similarity	NPC13175
0.5954	Remote Similarity	NPC475791
0.5952	Remote Similarity	NPC474576
0.5946	Remote Similarity	NPC313657
0.5941	Remote Similarity	NPC328494
0.5935	Remote Similarity	NPC469427
0.5935	Remote Similarity	NPC475278
0.5935	Remote Similarity	NPC304299
0.5935	Remote Similarity	NPC247776
0.5935	Remote Similarity	NPC469426
0.5935	Remote Similarity	NPC475266
0.5935	Remote Similarity	NPC71866
0.5935	Remote Similarity	NPC309450
0.592	Remote Similarity	NPC322966
0.5912	Remote Similarity	NPC328763
0.5896	Remote Similarity	NPC323720
0.5891	Remote Similarity	NPC469739
0.5886	Remote Similarity	NPC314358
0.5878	Remote Similarity	NPC475758
0.5873	Remote Similarity	NPC474593
0.5873	Remote Similarity	NPC475801
0.5868	Remote Similarity	NPC84128
0.5868	Remote Similarity	NPC53858
0.5868	Remote Similarity	NPC184473
0.5855	Remote Similarity	NPC287401
0.585	Remote Similarity	NPC473249
0.5839	Remote Similarity	NPC319766
0.5833	Remote Similarity	NPC233932
0.5823	Remote Similarity	NPC316008
0.5823	Remote Similarity	NPC313867
0.5806	Remote Similarity	NPC477539
0.5802	Remote Similarity	NPC162104
0.578	Remote Similarity	NPC471165
0.576	Remote Similarity	NPC477728
0.5759	Remote Similarity	NPC315283
0.5759	Remote Similarity	NPC314388
0.5753	Remote Similarity	NPC325750
0.5745	Remote Similarity	NPC471645
0.5714	Remote Similarity	NPC478024
0.5714	Remote Similarity	NPC471821
0.5714	Remote Similarity	NPC471820
0.5705	Remote Similarity	NPC477793
0.5705	Remote Similarity	NPC329919
0.5703	Remote Similarity	NPC477538
0.5697	Remote Similarity	NPC244509
0.5691	Remote Similarity	NPC477730
0.568	Remote Similarity	NPC471053
0.568	Remote Similarity	NPC471051
0.568	Remote Similarity	NPC471052
0.5673	Remote Similarity	NPC209463
0.5671	Remote Similarity	NPC473341
0.5669	Remote Similarity	NPC476259
0.5667	Remote Similarity	NPC313962
0.5662	Remote Similarity	NPC205176
0.566	Remote Similarity	NPC476978
0.5658	Remote Similarity	NPC314361
0.5656	Remote Similarity	NPC470783
0.5646	Remote Similarity	NPC16709
0.5645	Remote Similarity	NPC472351
0.5625	Remote Similarity	NPC315266
0.5621	Remote Similarity	NPC73655
0.562	Remote Similarity	NPC312315
0.5613	Remote Similarity	NPC230889
0.5612	Remote Similarity	NPC133729
0.5612	Remote Similarity	NPC326027
0.561	Remote Similarity	NPC284456
0.561	Remote Similarity	NPC6902
0.5607	Remote Similarity	NPC475204
0.5607	Remote Similarity	NPC475123
0.5606	Remote Similarity	NPC313821
0.5605	Remote Similarity	NPC315210
0.5605	Remote Similarity	NPC315848
0.5602	Remote Similarity	NPC477398
0.56	Remote Similarity	NPC26108

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 NPC470651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	82
0.1-0.2	504
0.2-0.3	4035
0.3-0.4	3851
0.4-0.5	606
0.5-0.6	68
0.6-0.7	4
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
0.64	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7916	Approved
0.6204	Remote Similarity	NPD7915	Approved
0.6172	Remote Similarity	NPD8038	Phase 2
0.6107	Remote Similarity	NPD3184	Approved
0.6107	Remote Similarity	NPD3182	Approved
0.6107	Remote Similarity	NPD3185	Approved
0.6107	Remote Similarity	NPD3183	Approved
0.5968	Remote Similarity	NPD3177	Phase 3
0.5952	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD8173	Phase 2
0.5948	Remote Similarity	NPD8172	Phase 2
0.594	Remote Similarity	NPD6122	Discontinued
0.5935	Remote Similarity	NPD7760	Phase 2
0.5935	Remote Similarity	NPD7759	Phase 2
0.5912	Remote Similarity	NPD3188	Approved
0.585	Remote Similarity	NPD7746	Phase 1
0.585	Remote Similarity	NPD7747	Phase 1
0.5827	Remote Similarity	NPD4261	Phase 1
0.5769	Remote Similarity	NPD8384	Approved
0.5738	Remote Similarity	NPD2683	Discontinued
0.5735	Remote Similarity	NPD1385	Discontinued
0.5692	Remote Similarity	NPD8394	Approved
0.5606	Remote Similarity	NPD3190	Approved
0.5606	Remote Similarity	NPD3191	Approved
0.5606	Remote Similarity	NPD3189	Approved
0.5605	Remote Similarity	NPD7761	Suspended

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