NPASS Compound

Structure

CID329216 OpenBabel06191716202D 84 85 0 0 1 0 0 0 0 0999 V2000 -2.5986 -16.0657 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 -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 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 -1.6068 -15.9377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7821 0.0110 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 -0.6735 -11.4512 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 -0.0667 -12.2461 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 -0.4517 -13.1690 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 0.1550 -13.9639 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 -0.2300 -14.8868 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 1.5706 -2.7979 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 -10.1659 -3.5261 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 -0.6684 2.3051 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2218 -15.0148 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.8658 -0.3896 0.0000 C 0 0 0 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 -9.1851 -3.3314 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 -6.9700 3.5740 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 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 -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 -8.3746 0.4815 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 -9.2795 -2.3358 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 -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 -5.9704 3.6010 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.5031 -1.8271 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 -9.1716 -1.3417 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 -8.8921 -4.2875 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 -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 -1.0409 3.2331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8285 -14.2199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4933 4.4262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8058 -2.9686 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 -9.1915 1.0583 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 -10.2795 -2.3291 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 -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 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 9 67 1 0 0 0 0 10 32 1 0 0 0 0 11 33 2 0 0 0 0 12 34 2 0 0 0 0 13 14 1 0 0 0 0 13 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 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 21 29 1 0 0 0 0 22 32 1 0 0 0 0 24 68 1 0 0 0 0 25 39 1 0 0 0 0 26 40 1 0 0 0 0 27 41 1 0 0 0 0 29 6 1 1 0 0 0 30 7 1 6 0 0 0 30 46 1 0 0 0 0 30 59 1 0 0 0 0 31 8 1 6 0 0 0 31 69 1 0 0 0 0 32 70 1 0 0 0 0 33 47 1 0 0 0 0 33 60 1 0 0 0 0 34 48 1 0 0 0 0 34 61 1 0 0 0 0 35 25 1 1 0 0 0 35 49 1 0 0 0 0 35 62 1 0 0 0 0 36 26 1 1 0 0 0 36 50 1 0 0 0 0 36 63 1 0 0 0 0 37 23 1 1 0 0 0 37 51 1 0 0 0 0 37 68 1 0 0 0 0 38 27 1 1 0 0 0 38 54 1 0 0 0 0 38 67 1 0 0 0 0 39 56 2 0 0 0 0 39 71 1 0 0 0 0 40 57 2 0 0 0 0 40 72 1 0 0 0 0 41 58 2 0 0 0 0 41 73 1 0 0 0 0 42 28 1 1 0 0 0 42 52 1 0 0 0 0 42 64 1 0 0 0 0 43 29 1 6 0 0 0 43 45 1 0 0 0 0 43 65 1 0 0 0 0 44 31 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 74 1 1 0 0 0 46 66 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 63 2 3 0 0 0 48 77 1 0 0 0 0 49 59 2 3 0 0 0 49 78 1 0 0 0 0 50 60 2 3 0 0 0 50 79 1 0 0 0 0 51 65 2 3 0 0 0 51 80 1 0 0 0 0 52 61 2 3 0 0 0 52 81 1 0 0 0 0 53 64 2 3 0 0 0 53 82 1 0 0 0 0 54 68 1 0 0 0 0 54 83 2 0 0 0 0 55 67 1 0 0 0 0 55 84 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1189.67
Volume:	1186.777
LogP:	0.434
LogD:	0.466
LogS:	-0.258
# Rotatable Bonds:	20
TPSA:	486.3
# H-Bond Aceptor:	29
# H-Bond Donor:	17
# Rings:	2
# Heavy Atoms:	29

MedChem Properties

QED Drug-Likeness Score:	0.036
Synthetic Accessibility Score:	7.703
Fsp3:	0.691
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-3.533
MDCK Permeability:	0.0007020689081400633
Pgp-inhibitor:	0.666
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.939
Plasma Protein Binding (PPB):	33.091697692871094%
Volume Distribution (VD):	0.385
Pgp-substrate:	33.412967681884766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	1.784
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.829
Carcinogencity:	0.123
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: NPC329216

Natural Product ID:	NPC329216
*Common Name:**	Minutissamide D
IUPAC Name:	2-[(3S,6S,9R,12S,15E,18S,21E,24S,27R,28R,31S)-3,18-bis(2-amino-2-oxoethyl)-15,21-di(ethylidene)-27-hydroxy-6-[(1R)-1-hydroxyethyl]-28-[(2S)-12-hydroxytetradecan-2-yl]-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 D
Standard InCHIKey:	QBOXPOZQNMGPJN-MVNQSCNZSA-N
Standard InCHI:	InChI=1S/C55H91N13O16/c1-10-32(70)22-19-17-15-13-14-16-18-21-29(6)43-45(74)53(82)64-42(28(4)5)52(81)61-34(12-3)48(77)63-36(26-40(57)72)50(79)60-33(11-2)47(76)62-35(25-39(56)71)49(78)59-30(7)46(75)66-44(31(8)69)55(84)67(9)38(27-41(58)73)54(83)68-24-20-23-37(68)51(80)65-43/h11-12,28-32,35-38,42-45,69-70,74H,10,13-27H2,1-9H3,(H2,56,71)(H2,57,72)(H2,58,73)(H,59,78)(H,60,79)(H,61,81)(H,62,76)(H,63,77)(H,64,82)(H,65,80)(H,66,75)/b33-11+,34-12+/t29-,30+,31+,32?,35-,36-,37-,38-,42-,43+,44-,45+/m0/s1
SMILES:	CCC(CCCCCCCCCC(C)C1C(C(=O)NC(C(=O)NC(=CC)C(=O)NC(C(=O)NC(=CC)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N2CCCC2C(=O)N1)CC(=O)N)C)C(C)O)C)CC(=O)N)CC(=O)N)C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1814284
PubChem CID:	53467423
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	=	22700.0	nM	PMID[549662]

☑ 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 NPC329216 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	102
0.1-0.2	1355
0.2-0.3	20582
0.3-0.4	17216
0.4-0.5	2594
0.5-0.6	668
0.6-0.7	140
0.7-0.8	29
0.8-0.85	1
0.85-0.9	2
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC296043
0.964	High Similarity	NPC160688
0.955	High Similarity	NPC470652
0.9298	High Similarity	NPC50520
0.9217	High Similarity	NPC470653
0.9217	High Similarity	NPC470654
0.9217	High Similarity	NPC470650
0.8983	High Similarity	NPC470655
0.8983	High Similarity	NPC470651
0.7719	Intermediate Similarity	NPC476877
0.7586	Intermediate Similarity	NPC476876
0.7581	Intermediate Similarity	NPC315188
0.7345	Intermediate Similarity	NPC134504
0.7345	Intermediate Similarity	NPC47076
0.7288	Intermediate Similarity	NPC241394
0.7273	Intermediate Similarity	NPC476875
0.7203	Intermediate Similarity	NPC128303
0.6885	Remote Similarity	NPC207820
0.6744	Remote Similarity	NPC469899
0.6744	Remote Similarity	NPC477237
0.6726	Remote Similarity	NPC275715
0.6667	Remote Similarity	NPC476156
0.6667	Remote Similarity	NPC316244
0.6667	Remote Similarity	NPC476117
0.6667	Remote Similarity	NPC476243
0.6667	Remote Similarity	NPC476137
0.6641	Remote Similarity	NPC477238
0.6639	Remote Similarity	NPC220234
0.6613	Remote Similarity	NPC171734
0.6606	Remote Similarity	NPC476302
0.6574	Remote Similarity	NPC31756
0.6541	Remote Similarity	NPC477462
0.6484	Remote Similarity	NPC471202
0.6484	Remote Similarity	NPC63191
0.648	Remote Similarity	NPC67009
0.6466	Remote Similarity	NPC273185
0.6443	Remote Similarity	NPC7817
0.6443	Remote Similarity	NPC475168
0.6434	Remote Similarity	NPC103391
0.6434	Remote Similarity	NPC472536
0.6396	Remote Similarity	NPC184473
0.6393	Remote Similarity	NPC188785
0.6387	Remote Similarity	NPC469739
0.6378	Remote Similarity	NPC251122
0.6341	Remote Similarity	NPC124554
0.6341	Remote Similarity	NPC5864
0.6341	Remote Similarity	NPC301148
0.6316	Remote Similarity	NPC477539
0.6316	Remote Similarity	NPC470902
0.6306	Remote Similarity	NPC470783
0.6299	Remote Similarity	NPC197743
0.6299	Remote Similarity	NPC297145
0.6293	Remote Similarity	NPC322966
0.6291	Remote Similarity	NPC315809
0.6291	Remote Similarity	NPC314050
0.6271	Remote Similarity	NPC315237
0.6271	Remote Similarity	NPC471098
0.6271	Remote Similarity	NPC62263
0.6271	Remote Similarity	NPC173763
0.6268	Remote Similarity	NPC287401
0.6268	Remote Similarity	NPC477400
0.6267	Remote Similarity	NPC2501
0.625	Remote Similarity	NPC53858
0.625	Remote Similarity	NPC84128
0.624	Remote Similarity	NPC124549
0.623	Remote Similarity	NPC475440
0.6214	Remote Similarity	NPC120335
0.6211	Remote Similarity	NPC328494
0.621	Remote Similarity	NPC475149
0.621	Remote Similarity	NPC471097
0.6204	Remote Similarity	NPC309525
0.6198	Remote Similarity	NPC473597
0.6195	Remote Similarity	NPC477730
0.6186	Remote Similarity	NPC474576
0.6179	Remote Similarity	NPC13175
0.6179	Remote Similarity	NPC475791
0.6164	Remote Similarity	NPC477401
0.6164	Remote Similarity	NPC477399
0.616	Remote Similarity	NPC198344
0.6159	Remote Similarity	NPC473249
0.6144	Remote Similarity	NPC122590
0.6143	Remote Similarity	NPC319766
0.614	Remote Similarity	NPC472351
0.6131	Remote Similarity	NPC36254
0.6111	Remote Similarity	NPC323720
0.6106	Remote Similarity	NPC6902
0.6106	Remote Similarity	NPC284456
0.6102	Remote Similarity	NPC474593
0.6102	Remote Similarity	NPC475801
0.6102	Remote Similarity	NPC477729
0.6098	Remote Similarity	NPC475758
0.6067	Remote Similarity	NPC314358
0.6063	Remote Similarity	NPC475637
0.6054	Remote Similarity	NPC476259
0.6047	Remote Similarity	NPC133729
0.604	Remote Similarity	NPC52748
0.6017	Remote Similarity	NPC155230
0.6	Remote Similarity	NPC313867
0.6	Remote Similarity	NPC470782
0.6	Remote Similarity	NPC316008
0.6	Remote Similarity	NPC315266
0.5983	Remote Similarity	NPC477728
0.5982	Remote Similarity	NPC312315
0.5962	Remote Similarity	NPC244509
0.5949	Remote Similarity	NPC469898
0.5933	Remote Similarity	NPC315283
0.5933	Remote Similarity	NPC314388
0.5917	Remote Similarity	NPC477538
0.5915	Remote Similarity	NPC313657
0.5909	Remote Similarity	NPC478024
0.5909	Remote Similarity	NPC314550
0.5878	Remote Similarity	NPC315210
0.5878	Remote Similarity	NPC315848
0.5877	Remote Similarity	NPC475542
0.5877	Remote Similarity	NPC23984
0.5871	Remote Similarity	NPC162104
0.5867	Remote Similarity	NPC176226
0.5859	Remote Similarity	NPC472616
0.5857	Remote Similarity	NPC46427
0.5849	Remote Similarity	NPC244336
0.5845	Remote Similarity	NPC313962
0.5843	Remote Similarity	NPC471165
0.5833	Remote Similarity	NPC314361
0.5827	Remote Similarity	NPC325750
0.5818	Remote Similarity	NPC126186
0.5814	Remote Similarity	NPC472615
0.5813	Remote Similarity	NPC114806
0.5813	Remote Similarity	NPC469901
0.5808	Remote Similarity	NPC469900
0.5793	Remote Similarity	NPC130309
0.5793	Remote Similarity	NPC473000
0.5786	Remote Similarity	NPC252878
0.5785	Remote Similarity	NPC476019
0.5782	Remote Similarity	NPC141050
0.5779	Remote Similarity	NPC471821
0.5779	Remote Similarity	NPC471820
0.5776	Remote Similarity	NPC73655
0.5775	Remote Similarity	NPC329919
0.5775	Remote Similarity	NPC477793
0.5762	Remote Similarity	NPC142761
0.5759	Remote Similarity	NPC477398
0.5759	Remote Similarity	NPC476268
0.575	Remote Similarity	NPC24617
0.5745	Remote Similarity	NPC6975
0.5745	Remote Similarity	NPC474371
0.5741	Remote Similarity	NPC471052
0.5741	Remote Similarity	NPC471051
0.5741	Remote Similarity	NPC471053
0.5739	Remote Similarity	NPC314466
0.5736	Remote Similarity	NPC205176
0.5732	Remote Similarity	NPC56685
0.5724	Remote Similarity	NPC476978
0.5714	Remote Similarity	NPC202521
0.5705	Remote Similarity	NPC473491
0.5704	Remote Similarity	NPC471645
0.5695	Remote Similarity	NPC304299
0.5695	Remote Similarity	NPC247776
0.5695	Remote Similarity	NPC475266
0.5695	Remote Similarity	NPC475278
0.5695	Remote Similarity	NPC309450
0.5695	Remote Similarity	NPC71866
0.5691	Remote Similarity	NPC38172
0.568	Remote Similarity	NPC313821
0.5678	Remote Similarity	NPC477199
0.5676	Remote Similarity	NPC161774
0.5676	Remote Similarity	NPC266888
0.5676	Remote Similarity	NPC256312
0.5676	Remote Similarity	NPC209156
0.5667	Remote Similarity	NPC324506
0.5667	Remote Similarity	NPC473495
0.5663	Remote Similarity	NPC475123
0.5663	Remote Similarity	NPC475204
0.5658	Remote Similarity	NPC77905
0.5655	Remote Similarity	NPC26108
0.5652	Remote Similarity	NPC470788
0.5649	Remote Similarity	NPC271562
0.5648	Remote Similarity	NPC195165
0.5643	Remote Similarity	NPC476990
0.5641	Remote Similarity	NPC235078
0.5636	Remote Similarity	NPC214532
0.5636	Remote Similarity	NPC470781
0.5636	Remote Similarity	NPC76297
0.5636	Remote Similarity	NPC477200
0.5636	Remote Similarity	NPC196007
0.5634	Remote Similarity	NPC315058
0.5633	Remote Similarity	NPC473341
0.5621	Remote Similarity	NPC50016
0.562	Remote Similarity	NPC209734
0.5614	Remote Similarity	NPC472999
0.561	Remote Similarity	NPC63931
0.5606	Remote Similarity	NPC15413
0.5606	Remote Similarity	NPC296143
0.56	Remote Similarity	NPC471265
0.56	Remote Similarity	NPC471264

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 NPC329216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	83
0.1-0.2	468
0.2-0.3	3845
0.3-0.4	3922
0.4-0.5	716
0.5-0.6	105
0.6-0.7	11
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
0.7064	Intermediate Similarity	NPD3723	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8038	Phase 2
0.646	Remote Similarity	NPD7760	Phase 2
0.646	Remote Similarity	NPD7759	Phase 2
0.6348	Remote Similarity	NPD3177	Phase 3
0.6325	Remote Similarity	NPD4261	Phase 1
0.6325	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6122	Discontinued
0.625	Remote Similarity	NPD2683	Discontinued
0.6159	Remote Similarity	NPD7747	Phase 1
0.6159	Remote Similarity	NPD7746	Phase 1
0.6027	Remote Similarity	NPD8172	Phase 2
0.6027	Remote Similarity	NPD8173	Phase 2
0.6018	Remote Similarity	NPD7763	Phase 2
0.6018	Remote Similarity	NPD7762	Phase 2
0.5857	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD1385	Discontinued
0.5772	Remote Similarity	NPD7761	Suspended
0.5772	Remote Similarity	NPD8394	Approved
0.5769	Remote Similarity	NPD6937	Approved
0.5766	Remote Similarity	NPD3159	Discontinued
0.576	Remote Similarity	NPD3715	Approved
0.576	Remote Similarity	NPD3714	Approved
0.576	Remote Similarity	NPD3713	Approved
0.5755	Remote Similarity	NPD7652	Discontinued
0.5755	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7623	Phase 3
0.5746	Remote Similarity	NPD1376	Discontinued
0.5743	Remote Similarity	NPD5767	Discontinued
0.5738	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD2645	Approved
0.5687	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.568	Remote Similarity	NPD3190	Approved
0.568	Remote Similarity	NPD3191	Approved
0.568	Remote Similarity	NPD3189	Approved
0.5669	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD2682	Approved
0.5649	Remote Similarity	NPD6676	Phase 2
0.5643	Remote Similarity	NPD1748	Approved
0.5643	Remote Similarity	NPD1806	Approved
0.5639	Remote Similarity	NPD1805	Phase 2
0.5639	Remote Similarity	NPD1804	Phase 2
0.5625	Remote Similarity	NPD7651	Approved
0.5606	Remote Similarity	NPD6693	Phase 3

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