NPASS Compound

Structure

NPC207820 OpenBabel07101719182D 81 81 0 0 1 0 0 0 0 0999 V2000 -5.6178 -2.7276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 9.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9852 9.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1192 10.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1192 6.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 -1.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8512 13.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8871 14.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 13.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2891 6.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7891 6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9230 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4230 2.7218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5211 11.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0211 10.2218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8512 16.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5689 -2.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2532 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 8.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7768 -1.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0337 -0.7713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0826 -1.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3395 -0.4112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3884 -0.7202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 -0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 6.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 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 -8.7173 15.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5833 15.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9852 15.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1192 9.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 4.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2532 6.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6942 -0.3601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9852 14.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2731 7.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 3.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2532 9.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3871 6.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 7.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 9.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2532 14.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 6.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9230 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 12.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 13.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9230 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 11.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1192 13.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 2.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2532 8.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 6.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 3.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 10.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 12.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 5.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.8512 15.5878 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 -9.5833 16.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 8.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 4.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 8.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 9.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2532 15.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 7.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 5.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 12.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 38 1 0 0 0 0 5 38 1 0 0 0 0 10 57 1 0 0 0 0 11 57 1 0 0 0 0 12 58 1 0 0 0 0 13 58 1 0 0 0 0 14 59 1 0 0 0 0 15 59 1 0 0 0 0 16 60 1 0 0 0 0 17 60 1 0 0 0 0 18 69 1 0 0 0 0 19 22 1 0 0 0 0 20 40 1 0 0 0 0 21 43 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 30 1 0 0 0 0 27 29 1 0 0 0 0 27 31 2 0 0 0 0 28 32 1 0 0 0 0 28 33 1 0 0 0 0 29 39 1 0 0 0 0 30 41 1 0 0 0 0 31 43 1 0 0 0 0 32 45 1 0 0 0 0 33 70 1 0 0 0 0 34 35 1 0 0 0 0 34 69 1 0 0 0 0 35 71 1 0 0 0 0 36 39 1 0 0 0 0 37 42 1 0 0 0 0 37 69 1 0 0 0 0 39 6 1 6 0 0 0 40 7 1 6 0 0 0 40 47 1 0 0 0 0 41 8 1 6 0 0 0 41 52 1 0 0 0 0 42 9 1 1 0 0 0 42 61 1 0 0 0 0 43 72 2 0 0 0 0 44 36 1 6 0 0 0 44 48 1 0 0 0 0 44 62 1 0 0 0 0 45 49 1 6 0 0 0 45 70 1 0 0 0 0 46 38 1 1 0 0 0 46 51 1 0 0 0 0 46 63 1 0 0 0 0 47 50 1 1 0 0 0 47 64 1 0 0 0 0 48 65 2 3 0 0 0 48 73 1 0 0 0 0 49 62 2 3 0 0 0 49 74 1 0 0 0 0 50 63 2 3 0 0 0 50 75 1 0 0 0 0 51 66 2 3 0 0 0 51 76 1 0 0 0 0 52 70 1 0 0 0 0 52 77 2 0 0 0 0 53 57 1 0 0 0 0 53 61 2 3 0 0 0 53 78 1 0 0 0 0 54 58 1 0 0 0 0 54 64 2 3 0 0 0 54 79 1 0 0 0 0 55 59 1 0 0 0 0 55 68 2 3 0 0 0 55 80 1 0 0 0 0 56 60 1 0 0 0 0 56 67 2 3 0 0 0 56 81 1 0 0 0 0 57 67 1 0 0 0 0 58 68 1 0 0 0 0 59 65 1 0 0 0 0 60 66 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.15
Volume:	315.764
LogP:	1.841
LogD:	2.691
LogS:	-1.547
# Rotatable Bonds:	4
TPSA:	50.72
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.911
Synthetic Accessibility Score:	2.601
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.977
MDCK Permeability:	1.7514055798528716e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.892
30% Bioavailability (F30%):	0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.651
Plasma Protein Binding (PPB):	52.01397705078125%
Volume Distribution (VD):	2.61
Pgp-substrate:	24.912168502807617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.282
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.417
CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.711
CYP2D6-inhibitor:	0.771
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.889

ADMET: Excretion

Clearance (CL):	10.334
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.343
Human Hepatotoxicity (H-HT):	0.486
Drug-inuced Liver Injury (DILI):	0.258
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.827
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.729
Carcinogencity:	0.082
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC207820

Natural Product ID:	NPC207820
*Common Name:**	Trichoderin A1
IUPAC Name:	(2S)-N-[(E,2S,4R)-1-[[1-[[1-[[(2S,3S)-1-[[(2S)-1-[[1-[[1-[[(2S)-1-[2-hydroxyethyl(methyl)amino]propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-4-methyl-1,8-dioxodec-6-en-2-yl]-1-[(2R)-2-methyldecanoyl]pyrrolidine-2-carboxamide
Synonyms:	Trichoderin A1
Standard InCHIKey:	UTAHJHKZUWFBTO-OIVUKLAESA-N
Standard InCHI:	InChI=1S/C60H108N10O11/c1-19-22-23-24-25-26-30-41(8)52(77)70-33-28-32-45(70)49(74)62-44(36-39(6)29-27-31-43(72)21-3)48(73)65-59(14,15)55(80)68-58(12,13)54(79)64-47(40(7)20-2)50(75)63-46(38(4)5)51(76)66-60(16,17)56(81)67-57(10,11)53(78)61-42(9)37-69(18)34-35-71/h27,31,38-42,44-47,71H,19-26,28-30,32-37H2,1-18H3,(H,61,78)(H,62,74)(H,63,75)(H,64,79)(H,65,73)(H,66,76)(H,67,81)(H,68,80)/b31-27+/t39-,40+,41-,42+,44+,45+,46+,47+/m1/s1
SMILES:	CCCCCCCC[C@H](C(=O)N1CCC[C@H]1C(=N[C@H](C(=NC(C(=NC(C(=N[C@H](C(=N[C@H](C(=NC(C(=NC(C(=N[C@H](CN(CCO)C)C)O)(C)C)O)(C)C)O)C(C)C)O)[C@H](CC)C)O)(C)C)O)(C)C)O)C[C@@H](C/C=C/C(=O)CC)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086383
PubChem CID:	46891554
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
NPO32631	Hypocrea sp.	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20483615]
NPO32631	Hypocrea sp.	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27328173]

☑ 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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	1.56	ug.mL-1	PMID[543543]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	0.16	ug.mL-1	PMID[543543]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	2.0	ug.mL-1	PMID[543543]

☑ 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 NPC207820 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	78
0.1-0.2	613
0.2-0.3	14105
0.3-0.4	18414
0.4-0.5	8053
0.5-0.6	1123
0.6-0.7	262
0.7-0.8	31
0.8-0.85	11
0.85-0.9	3
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8302	Intermediate Similarity	NPC476877
0.8148	Intermediate Similarity	NPC476876
0.8077	Intermediate Similarity	NPC47076
0.8077	Intermediate Similarity	NPC134504
0.7822	Intermediate Similarity	NPC324506
0.7797	Intermediate Similarity	NPC315188
0.7788	Intermediate Similarity	NPC476875
0.7398	Intermediate Similarity	NPC309525
0.7368	Intermediate Similarity	NPC171734
0.7213	Intermediate Similarity	NPC160688
0.72	Intermediate Similarity	NPC476156
0.72	Intermediate Similarity	NPC476137
0.72	Intermediate Similarity	NPC476243
0.72	Intermediate Similarity	NPC476117
0.7143	Intermediate Similarity	NPC472536
0.7143	Intermediate Similarity	NPC103391
0.7129	Intermediate Similarity	NPC476302
0.71	Intermediate Similarity	NPC31756
0.7043	Intermediate Similarity	NPC241394
0.704	Intermediate Similarity	NPC470654
0.704	Intermediate Similarity	NPC470653
0.704	Intermediate Similarity	NPC470650
0.6957	Remote Similarity	NPC128303
0.6942	Remote Similarity	NPC296043
0.693	Remote Similarity	NPC475149
0.693	Remote Similarity	NPC471097
0.6885	Remote Similarity	NPC329216
0.688	Remote Similarity	NPC200964
0.6861	Remote Similarity	NPC476978
0.685	Remote Similarity	NPC6975
0.6846	Remote Similarity	NPC120335
0.6814	Remote Similarity	NPC475758
0.6792	Remote Similarity	NPC477539
0.6789	Remote Similarity	NPC47230
0.6789	Remote Similarity	NPC17143
0.6767	Remote Similarity	NPC287401
0.6754	Remote Similarity	NPC13175
0.6754	Remote Similarity	NPC475791
0.6746	Remote Similarity	NPC273185
0.6742	Remote Similarity	NPC130309
0.6742	Remote Similarity	NPC255447
0.672	Remote Similarity	NPC470652
0.6719	Remote Similarity	NPC46427
0.6696	Remote Similarity	NPC469739
0.6694	Remote Similarity	NPC314550
0.6693	Remote Similarity	NPC202521
0.6667	Remote Similarity	NPC38172
0.6667	Remote Similarity	NPC220234
0.6667	Remote Similarity	NPC251122
0.6641	Remote Similarity	NPC252878
0.6639	Remote Similarity	NPC476276
0.662	Remote Similarity	NPC2501
0.6614	Remote Similarity	NPC476990
0.661	Remote Similarity	NPC476328
0.6593	Remote Similarity	NPC248283
0.6574	Remote Similarity	NPC322672
0.6571	Remote Similarity	NPC5620
0.6562	Remote Similarity	NPC50520
0.6552	Remote Similarity	NPC188785
0.6542	Remote Similarity	NPC475975
0.6538	Remote Similarity	NPC262880
0.6538	Remote Similarity	NPC247902
0.6525	Remote Similarity	NPC323720
0.6515	Remote Similarity	NPC41162
0.6514	Remote Similarity	NPC473525
0.65	Remote Similarity	NPC52748
0.6483	Remote Similarity	NPC122590
0.6481	Remote Similarity	NPC319913
0.6471	Remote Similarity	NPC141050
0.6455	Remote Similarity	NPC275715
0.6455	Remote Similarity	NPC155230
0.6449	Remote Similarity	NPC476133
0.6449	Remote Similarity	NPC98424
0.6449	Remote Similarity	NPC470884
0.6449	Remote Similarity	NPC472351
0.6449	Remote Similarity	NPC178662
0.6449	Remote Similarity	NPC92784
0.6446	Remote Similarity	NPC473578
0.6429	Remote Similarity	NPC239357
0.6429	Remote Similarity	NPC77905
0.6418	Remote Similarity	NPC200589
0.6418	Remote Similarity	NPC300315
0.6415	Remote Similarity	NPC184473
0.6412	Remote Similarity	NPC473249
0.641	Remote Similarity	NPC77703
0.6391	Remote Similarity	NPC319766
0.6389	Remote Similarity	NPC129666
0.6377	Remote Similarity	NPC471264
0.6377	Remote Similarity	NPC471265
0.6364	Remote Similarity	NPC470655
0.6364	Remote Similarity	NPC470651
0.6364	Remote Similarity	NPC135121
0.6364	Remote Similarity	NPC473495
0.6357	Remote Similarity	NPC269398
0.6357	Remote Similarity	NPC263493
0.6356	Remote Similarity	NPC124554
0.6356	Remote Similarity	NPC301148
0.6356	Remote Similarity	NPC5864
0.6343	Remote Similarity	NPC473322
0.6339	Remote Similarity	NPC477538
0.6338	Remote Similarity	NPC209509
0.6336	Remote Similarity	NPC474082
0.6336	Remote Similarity	NPC175726
0.6321	Remote Similarity	NPC470783
0.6319	Remote Similarity	NPC240848
0.6319	Remote Similarity	NPC471821
0.6319	Remote Similarity	NPC471820
0.6312	Remote Similarity	NPC161069
0.6309	Remote Similarity	NPC197743
0.6309	Remote Similarity	NPC297145
0.6303	Remote Similarity	NPC474563
0.6301	Remote Similarity	NPC162104
0.629	Remote Similarity	NPC469865
0.6286	Remote Similarity	NPC312315
0.6283	Remote Similarity	NPC471098
0.6283	Remote Similarity	NPC314500
0.6283	Remote Similarity	NPC62263
0.6283	Remote Similarity	NPC173763
0.6281	Remote Similarity	NPC251330
0.6277	Remote Similarity	NPC477400
0.627	Remote Similarity	NPC288629
0.6262	Remote Similarity	NPC6902
0.626	Remote Similarity	NPC36254
0.625	Remote Similarity	NPC329761
0.625	Remote Similarity	NPC469899
0.625	Remote Similarity	NPC124549
0.625	Remote Similarity	NPC225648
0.625	Remote Similarity	NPC474593
0.625	Remote Similarity	NPC205176
0.625	Remote Similarity	NPC475801
0.6241	Remote Similarity	NPC101719
0.624	Remote Similarity	NPC63191
0.624	Remote Similarity	NPC469597
0.624	Remote Similarity	NPC471202
0.623	Remote Similarity	NPC140251
0.623	Remote Similarity	NPC307903
0.623	Remote Similarity	NPC67009
0.6225	Remote Similarity	NPC469901
0.6224	Remote Similarity	NPC201244
0.6224	Remote Similarity	NPC477217
0.6214	Remote Similarity	NPC315848
0.6214	Remote Similarity	NPC315210
0.621	Remote Similarity	NPC474411
0.621	Remote Similarity	NPC474431
0.6207	Remote Similarity	NPC473597
0.6204	Remote Similarity	NPC473810
0.6202	Remote Similarity	NPC470546
0.6198	Remote Similarity	NPC271269
0.6198	Remote Similarity	NPC154601
0.6195	Remote Similarity	NPC474576
0.619	Remote Similarity	NPC471645
0.6186	Remote Similarity	NPC233932
0.6181	Remote Similarity	NPC314358
0.6181	Remote Similarity	NPC262077
0.6172	Remote Similarity	NPC285926
0.6172	Remote Similarity	NPC14672
0.6172	Remote Similarity	NPC315276
0.617	Remote Similarity	NPC476259
0.617	Remote Similarity	NPC239762
0.617	Remote Similarity	NPC477399
0.617	Remote Similarity	NPC163392
0.617	Remote Similarity	NPC477401
0.6168	Remote Similarity	NPC23984
0.6167	Remote Similarity	NPC198344
0.6165	Remote Similarity	NPC222466
0.6161	Remote Similarity	NPC322966
0.6159	Remote Similarity	NPC469898
0.6154	Remote Similarity	NPC91036
0.6138	Remote Similarity	NPC138775
0.6124	Remote Similarity	NPC470545
0.6122	Remote Similarity	NPC7817
0.6122	Remote Similarity	NPC475168
0.6117	Remote Similarity	NPC161774
0.6117	Remote Similarity	NPC266888
0.6117	Remote Similarity	NPC256312
0.6117	Remote Similarity	NPC209156
0.6111	Remote Similarity	NPC316008
0.6111	Remote Similarity	NPC313867
0.6111	Remote Similarity	NPC84128
0.6111	Remote Similarity	NPC315266
0.6111	Remote Similarity	NPC53858
0.6111	Remote Similarity	NPC284456
0.6103	Remote Similarity	NPC111428
0.6091	Remote Similarity	NPC477199
0.6084	Remote Similarity	NPC197682
0.6084	Remote Similarity	NPC139326
0.6084	Remote Similarity	NPC142761
0.6078	Remote Similarity	NPC97614
0.6068	Remote Similarity	NPC476449
0.6067	Remote Similarity	NPC469903
0.6056	Remote Similarity	NPC46098
0.6056	Remote Similarity	NPC307357
0.6056	Remote Similarity	NPC268841
0.6055	Remote Similarity	NPC235078
0.6054	Remote Similarity	NPC283783
0.605	Remote Similarity	NPC477964
0.6047	Remote Similarity	NPC470544
0.6047	Remote Similarity	NPC471109
0.6047	Remote Similarity	NPC474006
0.6047	Remote Similarity	NPC470300

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 NPC207820 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	79
0.1-0.2	321
0.2-0.3	2811
0.3-0.4	4421
0.4-0.5	1312
0.5-0.6	188
0.6-0.7	17
0.7-0.8	1
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
0.7115	Intermediate Similarity	NPD3723	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD8172	Phase 2
0.6741	Remote Similarity	NPD8173	Phase 2
0.6696	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7759	Phase 2
0.6481	Remote Similarity	NPD7760	Phase 2
0.6476	Remote Similarity	NPD7762	Phase 2
0.6476	Remote Similarity	NPD7763	Phase 2
0.6417	Remote Similarity	NPD6937	Approved
0.6415	Remote Similarity	NPD2683	Discontinued
0.6412	Remote Similarity	NPD7747	Phase 1
0.6412	Remote Similarity	NPD7746	Phase 1
0.635	Remote Similarity	NPD8416	Discontinued
0.6293	Remote Similarity	NPD8038	Phase 2
0.6269	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD2584	Suspended
0.6087	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8643	Discontinued
0.6054	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4261	Phase 1
0.6028	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD8323	Discontinued
0.6026	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2132	Phase 3
0.5985	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD7623	Phase 3
0.5956	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD6077	Discontinued
0.5944	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD4125	Approved
0.5938	Remote Similarity	NPD1000	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6122	Discontinued
0.589	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3713	Approved
0.5882	Remote Similarity	NPD3715	Approved
0.5882	Remote Similarity	NPD620	Approved
0.5882	Remote Similarity	NPD3714	Approved
0.5882	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD7613	Discontinued
0.5862	Remote Similarity	NPD7720	Phase 2
0.5852	Remote Similarity	NPD8273	Phase 1
0.5827	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD8065	Phase 2
0.5806	Remote Similarity	NPD7333	Discontinued
0.5802	Remote Similarity	NPD7641	Discontinued
0.5797	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3177	Phase 3
0.5786	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD2682	Approved
0.5764	Remote Similarity	NPD6901	Phase 3
0.5755	Remote Similarity	NPD3626	Phase 3
0.5755	Remote Similarity	NPD4175	Approved
0.5755	Remote Similarity	NPD4177	Approved
0.5753	Remote Similarity	NPD8076	Discontinued
0.5748	Remote Similarity	NPD6421	Discontinued
0.5748	Remote Similarity	NPD6420	Discontinued
0.5745	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD7011	Discontinued
0.5736	Remote Similarity	NPD1376	Discontinued
0.5735	Remote Similarity	NPD3071	Approved
0.5735	Remote Similarity	NPD3072	Approved
0.5735	Remote Similarity	NPD3073	Approved
0.5726	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD961	Discontinued
0.5714	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1689	Approved
0.5694	Remote Similarity	NPD6073	Approved
0.5694	Remote Similarity	NPD5725	Approved
0.5688	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7756	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD1125	Discovery
0.5667	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5662	Remote Similarity	NPD4762	Approved
0.5662	Remote Similarity	NPD4761	Approved
0.5652	Remote Similarity	NPD6792	Phase 3
0.5641	Remote Similarity	NPD790	Approved
0.5635	Remote Similarity	NPD2147	Approved
0.5634	Remote Similarity	NPD8415	Approved
0.562	Remote Similarity	NPD8041	Phase 2
0.5615	Remote Similarity	NPD8298	Phase 2
0.5613	Remote Similarity	NPD8417	Discontinued
0.5603	Remote Similarity	NPD4676	Approved
0.5603	Remote Similarity	NPD5263	Approved
0.56	Remote Similarity	NPD7602	Clinical (unspecified phase)

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