NPASS Compound

Structure

NPC470653 OpenBabel07101719172D 88 89 0 0 1 0 0 0 0 0999 V2000 -0.7783 -18.4504 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 -9.8933 1.0048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5871 -0.5823 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 -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 0.2134 -18.3224 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 -0.0667 -12.2461 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 -0.4517 -13.1690 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 0.1550 -13.9639 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 -0.2300 -14.8868 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 0.5985 -17.3995 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 0.3767 -15.6817 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 -9.7821 0.0110 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 -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 -0.0083 -16.6046 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 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 -8.8658 -0.3896 0.0000 C 0 0 1 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 -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 -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 -9.1716 -1.3417 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 -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 -10.4878 -4.4728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0001 -16.7326 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 6 33 1 0 0 0 0 11 71 1 0 0 0 0 12 88 1 0 0 0 0 13 24 1 0 0 0 0 14 39 2 0 0 0 0 15 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 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 23 30 1 0 0 0 0 24 38 1 0 0 0 0 25 34 1 0 0 0 0 26 38 1 0 0 0 0 28 29 1 0 0 0 0 29 43 1 0 0 0 0 30 72 1 0 0 0 0 31 44 1 0 0 0 0 34 7 1 1 0 0 0 35 8 1 6 0 0 0 35 51 1 0 0 0 0 35 63 1 0 0 0 0 36 9 1 6 0 0 0 36 73 1 0 0 0 0 37 10 1 6 0 0 0 37 88 1 0 0 0 0 38 74 2 0 0 0 0 39 52 1 0 0 0 0 39 64 1 0 0 0 0 40 28 1 1 0 0 0 40 53 1 0 0 0 0 40 65 1 0 0 0 0 41 27 1 1 0 0 0 41 54 1 0 0 0 0 41 72 1 0 0 0 0 42 31 1 1 0 0 0 42 59 1 0 0 0 0 42 71 1 0 0 0 0 43 61 2 0 0 0 0 43 75 1 0 0 0 0 44 62 2 0 0 0 0 44 76 1 0 0 0 0 45 32 1 1 0 0 0 45 56 1 0 0 0 0 45 66 1 0 0 0 0 46 33 1 1 0 0 0 46 55 1 0 0 0 0 46 67 1 0 0 0 0 47 34 1 6 0 0 0 47 50 1 0 0 0 0 47 68 1 0 0 0 0 48 36 1 1 0 0 0 48 57 1 0 0 0 0 48 69 1 0 0 0 0 49 37 1 1 0 0 0 49 60 1 0 0 0 0 49 70 1 0 0 0 0 50 58 1 0 0 0 0 50 77 1 1 0 0 0 51 70 2 3 0 0 0 51 78 1 0 0 0 0 52 69 2 3 0 0 0 52 79 1 0 0 0 0 53 63 2 3 0 0 0 53 80 1 0 0 0 0 54 68 2 3 0 0 0 54 81 1 0 0 0 0 55 64 2 3 0 0 0 55 82 1 0 0 0 0 56 65 2 3 0 0 0 56 83 1 0 0 0 0 57 66 2 3 0 0 0 57 84 1 0 0 0 0 58 67 2 3 0 0 0 58 85 1 0 0 0 0 59 72 1 0 0 0 0 59 86 2 0 0 0 0 60 71 1 0 0 0 0 60 87 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1246.75
Volume:	1264.897
LogP:	1.702
LogD:	1.14
LogS:	-1.096
# Rotatable Bonds:	24
TPSA:	445.79
# H-Bond Aceptor:	28
# H-Bond Donor:	14
# Rings:	2
# Heavy Atoms:	28

MedChem Properties

QED Drug-Likeness Score:	0.024
Synthetic Accessibility Score:	7.723
Fsp3:	0.75
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:	-3.816
MDCK Permeability:	0.00035772283445112407
Pgp-inhibitor:	0.963
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.894
Plasma Protein Binding (PPB):	42.738059997558594%
Volume Distribution (VD):	0.447
Pgp-substrate:	33.993125915527344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.031
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	1.4
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.69
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC470653

Natural Product ID:	NPC470653
*Common Name:**	Minutissamide H
IUPAC Name:	3-[(3S,6S,9R,12S,15S,18S,21E,24S,27R,28R,31S)-3-(2-amino-2-oxoethyl)-21-ethylidene-27-hydroxy-18-[(1R)-1-hydroxyethyl]-6-[(1R)-1-methoxyethyl]-4,9-dimethyl-2,5,8,11,14,17,20,23,26,30-decaoxo-28-[(2S)-13-oxohexadecan-2-yl]-15,24-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,29-decazabicyclo[29.3.0]tetratriacontan-12-yl]propanamide
Synonyms:	Minutissamide H
Standard InCHIKey:	NCWIBNGDUDTBCU-RAQHCFLESA-N
Standard InCHI:	InChI=1S/C60H102N12O16/c1-13-24-38(74)26-22-20-18-16-15-17-19-21-25-34(7)47-50(77)58(85)67-46(33(5)6)55(82)64-39(14-2)52(79)69-48(36(9)73)57(84)66-45(32(3)4)56(83)65-40(28-29-43(61)75)53(80)63-35(8)51(78)70-49(37(10)88-12)60(87)71(11)42(31-44(62)76)59(86)72-30-23-27-41(72)54(81)68-47/h14,32-37,40-42,45-50,73,77H,13,15-31H2,1-12H3,(H2,61,75)(H2,62,76)(H,63,80)(H,64,82)(H,65,83)(H,66,84)(H,67,85)(H,68,81)(H,69,79)(H,70,78)/b39-14+/t34-,35+,36+,37+,40-,41-,42-,45-,46-,47+,48-,49-,50+/m0/s1
SMILES:	CCCC(=O)CCCCCCCCCC[C@@H]([C@H]1N=C(O)[C@@H]2CCCN2C(=O)[C@H](CC(=N)O)N(C)C(=O)[C@@H](N=C(O)[C@@H](C)N=C(O)[C@@H](N=C([C@@H](N=C([C@@H](N=C(/C(=CC)/N=C([C@@H](N=C([C@@H]1O)O)C(C)C)O)O)[C@H](O)C)O)C(C)C)O)CCC(=N)O)[C@H](OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2148019
PubChem CID:	71451148
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	=	1100.0	nM	PMID[454848]

☑ 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 NPC470653 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	114
0.1-0.2	1178
0.2-0.3	18249
0.3-0.4	18365
0.4-0.5	3783
0.5-0.6	820
0.6-0.7	151
0.7-0.8	21
0.8-0.85	6
0.85-0.9	1
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470654
1.0	High Similarity	NPC470650
0.9649	High Similarity	NPC470652
0.9565	High Similarity	NPC160688
0.9217	High Similarity	NPC329216
0.913	High Similarity	NPC296043
0.9091	High Similarity	NPC470655
0.9091	High Similarity	NPC470651
0.8607	High Similarity	NPC50520
0.75	Intermediate Similarity	NPC134504
0.75	Intermediate Similarity	NPC47076
0.7308	Intermediate Similarity	NPC315188
0.7295	Intermediate Similarity	NPC241394
0.7213	Intermediate Similarity	NPC128303
0.7131	Intermediate Similarity	NPC476877
0.704	Intermediate Similarity	NPC207820
0.7023	Intermediate Similarity	NPC477237
0.702	Intermediate Similarity	NPC316244
0.7016	Intermediate Similarity	NPC476876
0.6917	Remote Similarity	NPC477238
0.6875	Remote Similarity	NPC477462
0.6875	Remote Similarity	NPC476875
0.6866	Remote Similarity	NPC273185
0.6838	Remote Similarity	NPC309525
0.6803	Remote Similarity	NPC220234
0.6772	Remote Similarity	NPC171734
0.6733	Remote Similarity	NPC2501
0.6714	Remote Similarity	NPC120335
0.6645	Remote Similarity	NPC314050
0.6645	Remote Similarity	NPC315809
0.6641	Remote Similarity	NPC67009
0.6641	Remote Similarity	NPC63191
0.6641	Remote Similarity	NPC471202
0.6601	Remote Similarity	NPC122590
0.6591	Remote Similarity	NPC472536
0.6591	Remote Similarity	NPC103391
0.6538	Remote Similarity	NPC297145
0.6538	Remote Similarity	NPC197743
0.6538	Remote Similarity	NPC251122
0.6528	Remote Similarity	NPC477400
0.6508	Remote Similarity	NPC5864
0.6508	Remote Similarity	NPC301148
0.6508	Remote Similarity	NPC124554
0.6471	Remote Similarity	NPC322966
0.6471	Remote Similarity	NPC7817
0.6471	Remote Similarity	NPC475168
0.6452	Remote Similarity	NPC470902
0.6446	Remote Similarity	NPC315237
0.6429	Remote Similarity	NPC188785
0.6429	Remote Similarity	NPC473249
0.6419	Remote Similarity	NPC477399
0.6419	Remote Similarity	NPC477401
0.6406	Remote Similarity	NPC124549
0.6406	Remote Similarity	NPC323720
0.64	Remote Similarity	NPC52748
0.6397	Remote Similarity	NPC469899
0.6348	Remote Similarity	NPC476302
0.6343	Remote Similarity	NPC471645
0.6333	Remote Similarity	NPC275715
0.6328	Remote Similarity	NPC198344
0.6311	Remote Similarity	NPC471098
0.6311	Remote Similarity	NPC173763
0.6311	Remote Similarity	NPC62263
0.6286	Remote Similarity	NPC36254
0.6281	Remote Similarity	NPC477729
0.627	Remote Similarity	NPC475440
0.6261	Remote Similarity	NPC476156
0.6261	Remote Similarity	NPC476117
0.6261	Remote Similarity	NPC476243
0.6261	Remote Similarity	NPC476137
0.625	Remote Similarity	NPC475149
0.625	Remote Similarity	NPC471097
0.6231	Remote Similarity	NPC475637
0.623	Remote Similarity	NPC474576
0.6218	Remote Similarity	NPC162104
0.6212	Remote Similarity	NPC133729
0.6207	Remote Similarity	NPC314361
0.6186	Remote Similarity	NPC472351
0.6181	Remote Similarity	NPC313657
0.6174	Remote Similarity	NPC31756
0.616	Remote Similarity	NPC469739
0.6154	Remote Similarity	NPC53858
0.6154	Remote Similarity	NPC84128
0.6148	Remote Similarity	NPC474593
0.6148	Remote Similarity	NPC475801
0.6145	Remote Similarity	NPC328494
0.6129	Remote Similarity	NPC471820
0.6129	Remote Similarity	NPC471821
0.6111	Remote Similarity	NPC473597
0.6104	Remote Similarity	NPC314358
0.6099	Remote Similarity	NPC325750
0.6098	Remote Similarity	NPC476019
0.6094	Remote Similarity	NPC475791
0.6094	Remote Similarity	NPC13175
0.6078	Remote Similarity	NPC476978
0.6074	Remote Similarity	NPC471052
0.6074	Remote Similarity	NPC471053
0.6074	Remote Similarity	NPC471051
0.6053	Remote Similarity	NPC309450
0.6053	Remote Similarity	NPC247776
0.6053	Remote Similarity	NPC71866
0.6053	Remote Similarity	NPC475266
0.6053	Remote Similarity	NPC304299
0.6053	Remote Similarity	NPC475278
0.6042	Remote Similarity	NPC329919
0.6042	Remote Similarity	NPC477793
0.6039	Remote Similarity	NPC316008
0.6039	Remote Similarity	NPC313867
0.6031	Remote Similarity	NPC472616
0.6026	Remote Similarity	NPC315848
0.6026	Remote Similarity	NPC315210
0.6017	Remote Similarity	NPC184473
0.6016	Remote Similarity	NPC475758
0.6014	Remote Similarity	NPC474371
0.6013	Remote Similarity	NPC142761
0.6	Remote Similarity	NPC477398
0.5987	Remote Similarity	NPC476259
0.5985	Remote Similarity	NPC472615
0.5976	Remote Similarity	NPC26108
0.5976	Remote Similarity	NPC471165
0.5974	Remote Similarity	NPC314388
0.5974	Remote Similarity	NPC315283
0.5973	Remote Similarity	NPC287401
0.5959	Remote Similarity	NPC319766
0.5956	Remote Similarity	NPC314550
0.595	Remote Similarity	NPC477539
0.5946	Remote Similarity	NPC120420
0.5935	Remote Similarity	NPC5620
0.5932	Remote Similarity	NPC23984
0.5932	Remote Similarity	NPC470783
0.5926	Remote Similarity	NPC327517
0.5926	Remote Similarity	NPC321485
0.5926	Remote Similarity	NPC319334
0.5926	Remote Similarity	NPC322372
0.5926	Remote Similarity	NPC317377
0.5909	Remote Similarity	NPC176226
0.5906	Remote Similarity	NPC99864
0.5902	Remote Similarity	NPC477728
0.5899	Remote Similarity	NPC209734
0.5897	Remote Similarity	NPC312315
0.5896	Remote Similarity	NPC475150
0.5882	Remote Similarity	NPC284456
0.5882	Remote Similarity	NPC6902
0.5875	Remote Similarity	NPC473341
0.5872	Remote Similarity	NPC269750
0.5872	Remote Similarity	NPC194671
0.586	Remote Similarity	NPC135121
0.5854	Remote Similarity	NPC324506
0.584	Remote Similarity	NPC477538
0.5839	Remote Similarity	NPC478024
0.5833	Remote Similarity	NPC315266
0.5833	Remote Similarity	NPC235078
0.5833	Remote Similarity	NPC477730
0.5833	Remote Similarity	NPC477518
0.5828	Remote Similarity	NPC248283
0.5821	Remote Similarity	NPC271562
0.5818	Remote Similarity	NPC73655
0.5806	Remote Similarity	NPC155230
0.5802	Remote Similarity	NPC244509
0.5799	Remote Similarity	NPC475123
0.5799	Remote Similarity	NPC475204
0.5798	Remote Similarity	NPC475542
0.5792	Remote Similarity	NPC323662
0.5789	Remote Similarity	NPC74035
0.5789	Remote Similarity	NPC205176
0.5786	Remote Similarity	NPC316325
0.5786	Remote Similarity	NPC129666
0.5782	Remote Similarity	NPC313962
0.5779	Remote Similarity	NPC46098
0.5779	Remote Similarity	NPC307357
0.5779	Remote Similarity	NPC268841
0.5763	Remote Similarity	NPC478017
0.5763	Remote Similarity	NPC315131
0.5763	Remote Similarity	NPC315535
0.5759	Remote Similarity	NPC145113
0.5758	Remote Similarity	NPC469901
0.5756	Remote Similarity	NPC469900
0.5745	Remote Similarity	NPC296361
0.5742	Remote Similarity	NPC269398
0.5742	Remote Similarity	NPC263493
0.5739	Remote Similarity	NPC471050
0.5739	Remote Similarity	NPC471049
0.5739	Remote Similarity	NPC471048
0.5739	Remote Similarity	NPC294951
0.5738	Remote Similarity	NPC227051
0.5736	Remote Similarity	NPC313821
0.5733	Remote Similarity	NPC130309
0.5732	Remote Similarity	NPC477519
0.5732	Remote Similarity	NPC477217
0.5732	Remote Similarity	NPC201244
0.5732	Remote Similarity	NPC209509
0.5725	Remote Similarity	NPC469865
0.5714	Remote Similarity	NPC7905
0.5714	Remote Similarity	NPC476133
0.5714	Remote Similarity	NPC98424
0.5714	Remote Similarity	NPC92784
0.5714	Remote Similarity	NPC315652
0.5714	Remote Similarity	NPC178662
0.5714	Remote Similarity	NPC470884
0.5707	Remote Similarity	NPC477552

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 NPC470653 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	535
0.2-0.3	3505
0.3-0.4	4076
0.4-0.5	797
0.5-0.6	132
0.6-0.7	13
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
0.6833	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8038	Phase 2
0.6429	Remote Similarity	NPD7746	Phase 1
0.6429	Remote Similarity	NPD7747	Phase 1
0.6395	Remote Similarity	NPD8172	Phase 2
0.6395	Remote Similarity	NPD8173	Phase 2
0.625	Remote Similarity	NPD3177	Phase 3
0.623	Remote Similarity	NPD4261	Phase 1
0.6218	Remote Similarity	NPD7759	Phase 2
0.6218	Remote Similarity	NPD7760	Phase 2
0.608	Remote Similarity	NPD8394	Approved
0.6077	Remote Similarity	NPD6122	Discontinued
0.6063	Remote Similarity	NPD3714	Approved
0.6063	Remote Similarity	NPD3713	Approved
0.6063	Remote Similarity	NPD3715	Approved
0.6028	Remote Similarity	NPD7623	Phase 3
0.6028	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD2683	Discontinued
0.6015	Remote Similarity	NPD6693	Phase 3
0.5987	Remote Similarity	NPD6077	Discontinued
0.5973	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.594	Remote Similarity	NPD6937	Approved
0.5929	Remote Similarity	NPD2132	Phase 3
0.5923	Remote Similarity	NPD7651	Approved
0.5912	Remote Similarity	NPD1376	Discontinued
0.5906	Remote Similarity	NPD8415	Approved
0.587	Remote Similarity	NPD7916	Approved
0.587	Remote Similarity	NPD7915	Approved
0.5865	Remote Similarity	NPD1385	Discontinued
0.5845	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD6421	Discontinued
0.5798	Remote Similarity	NPD7762	Phase 2
0.5798	Remote Similarity	NPD7763	Phase 2
0.5793	Remote Similarity	NPD8273	Phase 1
0.5789	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD7500	Approved
0.5766	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD3189	Approved
0.5736	Remote Similarity	NPD3191	Approved
0.5736	Remote Similarity	NPD3190	Approved
0.5735	Remote Similarity	NPD6413	Approved
0.5725	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2633	Phase 1
0.5714	Remote Similarity	NPD2682	Approved
0.5714	Remote Similarity	NPD7761	Suspended
0.5706	Remote Similarity	NPD8414	Discontinued
0.5704	Remote Similarity	NPD8140	Approved
0.5693	Remote Similarity	NPD1804	Phase 2
0.5693	Remote Similarity	NPD1805	Phase 2
0.5685	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5683	Remote Similarity	NPD8298	Phase 2
0.5674	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD6935	Phase 3
0.5669	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD1689	Approved
0.5636	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD7756	Clinical (unspecified phase)
0.563	Remote Similarity	NPD1428	Phase 2
0.56	Remote Similarity	NPD2101	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