NPASS Compound

Structure

CID197736 OpenBabel06191715582D 71 75 0 0 1 0 0 0 0 0999 V2000 -6.5705 6.7003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5618 -7.4059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6157 4.0516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0376 -0.2863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5705 6.7003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0705 5.8343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9925 -1.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9925 -2.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0705 7.5663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6831 -5.2846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0705 2.3702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7865 -8.6306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0705 5.8343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2689 -6.6988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3300 1.5481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7520 2.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0086 0.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4305 3.1641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2646 2.5460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6866 1.2193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7712 3.9160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3492 -0.1506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0705 2.3702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8888 -7.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5705 4.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7853 -4.5081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8223 3.4429 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2443 0.3225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0705 5.8343 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5705 4.9682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9925 -1.2029 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9925 -2.9350 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5705 6.7003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7172 -5.0257 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0705 2.3702 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8206 -8.3718 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0705 5.8343 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0101 -5.7328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5705 1.5041 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1476 -8.8201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0705 5.8343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5705 4.9682 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0442 -5.4740 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8743 4.3582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5477 -0.5929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5705 3.2362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5959 -7.1471 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5705 4.9682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4925 -2.0689 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5705 1.5041 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1135 -9.0789 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0705 4.1022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4925 -0.3369 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4925 -3.8010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0705 0.6381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4405 -9.5272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1331 5.3242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2888 -1.5589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0705 4.1022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4925 -2.0689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0705 0.6381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3723 -10.0448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5010 -3.6705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5705 6.7003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5705 3.2362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5618 -7.4059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0705 4.1022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3371 -6.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8765 4.4236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5455 -0.6583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4584 -4.0598 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 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 22 2 0 0 0 0 18 21 2 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 44 1 0 0 0 0 22 45 1 0 0 0 0 23 39 1 0 0 0 0 23 46 1 0 0 0 0 24 40 1 0 0 0 0 24 47 1 0 0 0 0 25 41 2 0 0 0 0 25 42 1 0 0 0 0 26 43 1 0 0 0 0 26 54 1 0 0 0 0 27 3 1 6 0 0 0 27 52 1 0 0 0 0 28 4 1 6 0 0 0 28 53 1 0 0 0 0 29 5 1 1 0 0 0 29 41 1 0 0 0 0 29 48 1 0 0 0 0 30 6 1 6 0 0 0 30 48 1 0 0 0 0 31 7 1 1 0 0 0 31 49 1 0 0 0 0 32 8 1 6 0 0 0 32 49 1 0 0 0 0 32 54 1 0 0 0 0 33 9 1 1 0 0 0 33 37 1 0 0 0 0 33 64 1 0 0 0 0 34 10 1 6 0 0 0 34 38 1 0 0 0 0 34 71 1 0 0 0 0 35 11 1 1 0 0 0 35 50 1 0 0 0 0 35 65 1 0 0 0 0 36 12 1 1 0 0 0 36 51 1 0 0 0 0 36 66 1 0 0 0 0 37 13 1 6 0 0 0 37 42 1 0 0 0 0 38 14 1 1 0 0 0 38 43 1 0 0 0 0 39 50 1 0 0 0 0 39 55 1 1 0 0 0 40 51 1 0 0 0 0 40 56 1 1 0 0 0 41 64 1 0 0 0 0 42 67 1 1 0 0 0 43 68 1 6 0 0 0 44 57 2 0 0 0 0 44 69 1 0 0 0 0 45 58 2 0 0 0 0 45 70 1 0 0 0 0 46 65 1 0 0 0 0 46 67 1 6 0 0 0 47 66 1 0 0 0 0 47 68 1 6 0 0 0 48 59 1 1 0 0 0 49 60 1 6 0 0 0 50 61 1 1 0 0 0 51 62 1 1 0 0 0 52 30 1 1 0 0 0 52 69 1 0 0 0 0 53 31 1 1 0 0 0 53 70 1 0 0 0 0 54 63 1 1 0 0 0 54 71 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1006.59
Volume:	1030.736
LogP:	6.096
LogD:	4.847
LogS:	-4.838
# Rotatable Bonds:	14
TPSA:	249.59
# H-Bond Aceptor:	17
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	7.585
Fsp3:	0.778
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.37
MDCK Permeability:	0.00039489578921347857
Pgp-inhibitor:	1.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.835
20% Bioavailability (F20%):	0.189
30% Bioavailability (F30%):	0.696

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	88.10501098632812%
Volume Distribution (VD):	0.89
Pgp-substrate:	5.921917915344238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.614
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	5.369
Half-life (T1/2):	0.054

ADMET: Toxicity

hERG Blockers:	0.676
Human Hepatotoxicity (H-HT):	0.513
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.948
Carcinogencity:	0.115
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC197736

Natural Product ID:	NPC197736
*Common Name:**	11',12'-Dehydroelaiophylin
IUPAC Name:	(3E,5E,7S,8S,11E,13E,15S,16S)-8-[(2S,3R,4S)-4-[(2R,4R,5R,6R)-4-[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-ethyl-2-hydroxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-16-[(2S,3R,4S)-4-[(2R,3R,4S)-4-[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2-methyl-3,4-dihydro-2H-pyran-6-yl]-3-hydroxypentan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
Synonyms:
Standard InCHIKey:	OSJLHWZHXOEYPJ-JRNNISHJSA-N
Standard InCHI:	InChI=1S/C54H86O17/c1-13-37-33(9)64-41(25-42(37)67-46-23-39(55)50(61)35(11)65-46)29(5)48(59)30(6)52-27(3)19-15-17-22-45(58)70-53(28(4)20-16-18-21-44(57)69-52)31(7)49(60)32(8)54(63)26-43(38(14-2)34(10)71-54)68-47-24-40(56)51(62)36(12)66-47/h15-22,25,27-40,42-43,46-53,55-56,59-63H,13-14,23-24,26H2,1-12H3/b19-15+,20-16+,21-18+,22-17+/t27-,28-,29+,30-,31-,32-,33+,34+,35-,36-,37+,38+,39-,40-,42+,43+,46-,47-,48-,49+,50+,51+,52-,53-,54+/m0/s1
SMILES:	CC[C@@H]1[C@@H](C)OC(=C[C@H]1O[C@H]1C[C@@H]([C@@H]([C@H](C)O1)O)O)[C@@H](C)[C@@H]([C@H](C)[C@@H]1[C@@H](C)/C=C/C=C/C(=O)O[C@@H]([C@@H](C)/C=C/C=C/C(=O)O1)[C@@H](C)[C@H]([C@H](C)[C@]1(C[C@H]([C@H](CC)[C@@H](C)O1)O[C@H]1C[C@@H]([C@@H]([C@H](C)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3086647
PubChem CID:	72945493
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32916	Streptomyces sp. 7-145	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24164206]

☑ 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	22

Activity Type	# Activity
NON-MOLECULAR	1
Organism	21

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3495	Organism	Morganella morganii	Morganella morganii	MIC	>	64.0	ug.mL-1	PMID[556245]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	64.0	ug.mL-1	PMID[556245]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	64.0	ug.mL-1	PMID[556245]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	64.0	ug.mL-1	PMID[556245]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[556245]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	64.0	ug.mL-1	PMID[556245]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	64.0	ug.mL-1	PMID[556245]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	>	64.0	ug.mL-1	PMID[556245]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64.0	ug.mL-1	PMID[556245]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	4.0	ug.mL-1	PMID[556245]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[556245]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[556245]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2.0	ug.mL-1	PMID[556245]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	2.0	ug.mL-1	PMID[556245]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	=	2.0	ug.mL-1	PMID[556245]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[556245]

☑ 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 NPC197736 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	217
0.1-0.2	1303
0.2-0.3	4232
0.3-0.4	8707
0.4-0.5	14316
0.5-0.6	9635
0.6-0.7	3553
0.7-0.8	682
0.8-0.85	36
0.85-0.9	4
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC475157
0.9583	High Similarity	NPC471637
0.9583	High Similarity	NPC154132
0.9583	High Similarity	NPC2313
0.9583	High Similarity	NPC475655
0.9583	High Similarity	NPC57586
0.92	High Similarity	NPC315070
0.8878	High Similarity	NPC475332
0.875	High Similarity	NPC476075
0.875	High Similarity	NPC476084
0.8571	High Similarity	NPC159698
0.8571	High Similarity	NPC133625
0.8557	High Similarity	NPC114172
0.8557	High Similarity	NPC471324
0.8557	High Similarity	NPC206679
0.8469	Intermediate Similarity	NPC238090
0.8469	Intermediate Similarity	NPC472195
0.8469	Intermediate Similarity	NPC159092
0.8469	Intermediate Similarity	NPC472196
0.8469	Intermediate Similarity	NPC109406
0.84	Intermediate Similarity	NPC288350
0.84	Intermediate Similarity	NPC173329
0.8367	Intermediate Similarity	NPC110072
0.8351	Intermediate Similarity	NPC285588
0.8283	Intermediate Similarity	NPC320552
0.8265	Intermediate Similarity	NPC327253
0.8229	Intermediate Similarity	NPC208473
0.82	Intermediate Similarity	NPC256368
0.8173	Intermediate Similarity	NPC201191
0.8144	Intermediate Similarity	NPC313658
0.8144	Intermediate Similarity	NPC316138
0.8131	Intermediate Similarity	NPC193765
0.8131	Intermediate Similarity	NPC473807
0.8119	Intermediate Similarity	NPC170204
0.8119	Intermediate Similarity	NPC469543
0.8103	Intermediate Similarity	NPC179261
0.8087	Intermediate Similarity	NPC219804
0.8039	Intermediate Similarity	NPC255410
0.8021	Intermediate Similarity	NPC473308
0.8021	Intermediate Similarity	NPC266718
0.8	Intermediate Similarity	NPC251026
0.7961	Intermediate Similarity	NPC120299
0.7959	Intermediate Similarity	NPC475186
0.7959	Intermediate Similarity	NPC199382
0.7959	Intermediate Similarity	NPC118077
0.7944	Intermediate Similarity	NPC476740
0.7944	Intermediate Similarity	NPC476738
0.7941	Intermediate Similarity	NPC300710
0.7921	Intermediate Similarity	NPC61201
0.7917	Intermediate Similarity	NPC473315
0.7917	Intermediate Similarity	NPC142111
0.79	Intermediate Similarity	NPC202886
0.79	Intermediate Similarity	NPC177668
0.7895	Intermediate Similarity	NPC469469
0.7895	Intermediate Similarity	NPC8538
0.7895	Intermediate Similarity	NPC184208
0.7885	Intermediate Similarity	NPC475653
0.7885	Intermediate Similarity	NPC203627
0.7843	Intermediate Similarity	NPC477345
0.7843	Intermediate Similarity	NPC294293
0.7843	Intermediate Similarity	NPC477348
0.7843	Intermediate Similarity	NPC238264
0.783	Intermediate Similarity	NPC222062
0.7822	Intermediate Similarity	NPC472124
0.7822	Intermediate Similarity	NPC477749
0.7822	Intermediate Similarity	NPC472125
0.7822	Intermediate Similarity	NPC472126
0.78	Intermediate Similarity	NPC477748
0.78	Intermediate Similarity	NPC133450
0.7778	Intermediate Similarity	NPC82251
0.7757	Intermediate Similarity	NPC475367
0.7757	Intermediate Similarity	NPC234304
0.7757	Intermediate Similarity	NPC284929
0.7757	Intermediate Similarity	NPC309398
0.7757	Intermediate Similarity	NPC118761
0.7757	Intermediate Similarity	NPC474581
0.7757	Intermediate Similarity	NPC197541
0.7757	Intermediate Similarity	NPC473816
0.7757	Intermediate Similarity	NPC267869
0.7755	Intermediate Similarity	NPC471494
0.7745	Intermediate Similarity	NPC320089
0.7739	Intermediate Similarity	NPC219656
0.7736	Intermediate Similarity	NPC476611
0.7736	Intermediate Similarity	NPC219038
0.7727	Intermediate Similarity	NPC315836
0.7727	Intermediate Similarity	NPC313668
0.7723	Intermediate Similarity	NPC3952
0.7723	Intermediate Similarity	NPC6414
0.7723	Intermediate Similarity	NPC307699
0.7723	Intermediate Similarity	NPC303451
0.7723	Intermediate Similarity	NPC473311
0.7708	Intermediate Similarity	NPC315731
0.77	Intermediate Similarity	NPC470137
0.7692	Intermediate Similarity	NPC473765
0.7692	Intermediate Similarity	NPC473605
0.7692	Intermediate Similarity	NPC475540
0.7692	Intermediate Similarity	NPC475525
0.7692	Intermediate Similarity	NPC475241
0.7692	Intermediate Similarity	NPC476066
0.7692	Intermediate Similarity	NPC475375
0.7692	Intermediate Similarity	NPC475164
0.7692	Intermediate Similarity	NPC475593
0.7685	Intermediate Similarity	NPC469869
0.7684	Intermediate Similarity	NPC139712
0.7679	Intermediate Similarity	NPC317460
0.7679	Intermediate Similarity	NPC328074
0.7679	Intermediate Similarity	NPC321272
0.7679	Intermediate Similarity	NPC470025
0.7677	Intermediate Similarity	NPC311163
0.7672	Intermediate Similarity	NPC135369
0.767	Intermediate Similarity	NPC472198
0.7664	Intermediate Similarity	NPC473596
0.7664	Intermediate Similarity	NPC471599
0.7658	Intermediate Similarity	NPC316708
0.7652	Intermediate Similarity	NPC470515
0.7647	Intermediate Similarity	NPC477349
0.7647	Intermediate Similarity	NPC472199
0.7647	Intermediate Similarity	NPC472197
0.7642	Intermediate Similarity	NPC244878
0.7611	Intermediate Similarity	NPC470027
0.7611	Intermediate Similarity	NPC473159
0.7607	Intermediate Similarity	NPC233500
0.7607	Intermediate Similarity	NPC170880
0.7604	Intermediate Similarity	NPC470147
0.7604	Intermediate Similarity	NPC133226
0.7604	Intermediate Similarity	NPC163362
0.7604	Intermediate Similarity	NPC127295
0.76	Intermediate Similarity	NPC125142
0.7589	Intermediate Similarity	NPC470026
0.7589	Intermediate Similarity	NPC17791
0.7589	Intermediate Similarity	NPC126897
0.7589	Intermediate Similarity	NPC297945
0.7586	Intermediate Similarity	NPC470911
0.7586	Intermediate Similarity	NPC470914
0.7586	Intermediate Similarity	NPC470517
0.7586	Intermediate Similarity	NPC470915
0.7576	Intermediate Similarity	NPC470124
0.757	Intermediate Similarity	NPC20673
0.757	Intermediate Similarity	NPC198992
0.7549	Intermediate Similarity	NPC117596
0.7547	Intermediate Similarity	NPC151093
0.7545	Intermediate Similarity	NPC109376
0.7542	Intermediate Similarity	NPC196130
0.7525	Intermediate Similarity	NPC248312
0.7524	Intermediate Similarity	NPC143446
0.7523	Intermediate Similarity	NPC470768
0.752	Intermediate Similarity	NPC127656
0.75	Intermediate Similarity	NPC44682
0.75	Intermediate Similarity	NPC47220
0.75	Intermediate Similarity	NPC470148
0.75	Intermediate Similarity	NPC470149
0.75	Intermediate Similarity	NPC186332
0.75	Intermediate Similarity	NPC195510
0.75	Intermediate Similarity	NPC180725
0.75	Intermediate Similarity	NPC13171
0.75	Intermediate Similarity	NPC163409
0.7478	Intermediate Similarity	NPC207637
0.7477	Intermediate Similarity	NPC224660
0.7477	Intermediate Similarity	NPC470024
0.7477	Intermediate Similarity	NPC392
0.7477	Intermediate Similarity	NPC306344
0.7477	Intermediate Similarity	NPC177524
0.7477	Intermediate Similarity	NPC22149
0.7477	Intermediate Similarity	NPC255677
0.7477	Intermediate Similarity	NPC219900
0.7475	Intermediate Similarity	NPC475035
0.7474	Intermediate Similarity	NPC474026
0.7458	Intermediate Similarity	NPC170084
0.7458	Intermediate Similarity	NPC183353
0.7458	Intermediate Similarity	NPC469812
0.7458	Intermediate Similarity	NPC476204
0.7456	Intermediate Similarity	NPC287075
0.7455	Intermediate Similarity	NPC470767
0.7455	Intermediate Similarity	NPC172867
0.7455	Intermediate Similarity	NPC239961
0.7455	Intermediate Similarity	NPC470763
0.7453	Intermediate Similarity	NPC309503
0.7453	Intermediate Similarity	NPC476612
0.7453	Intermediate Similarity	NPC91197
0.7453	Intermediate Similarity	NPC278506
0.7453	Intermediate Similarity	NPC476613
0.7453	Intermediate Similarity	NPC239547
0.7453	Intermediate Similarity	NPC96597
0.7453	Intermediate Similarity	NPC155319
0.7453	Intermediate Similarity	NPC125551
0.7449	Intermediate Similarity	NPC477385
0.7449	Intermediate Similarity	NPC477390
0.7429	Intermediate Similarity	NPC101051
0.7426	Intermediate Similarity	NPC475037
0.7417	Intermediate Similarity	NPC471090
0.7407	Intermediate Similarity	NPC4637
0.7407	Intermediate Similarity	NPC98859
0.7407	Intermediate Similarity	NPC28304
0.7407	Intermediate Similarity	NPC280991
0.7407	Intermediate Similarity	NPC298255
0.7404	Intermediate Similarity	NPC280390
0.7404	Intermediate Similarity	NPC189651
0.7404	Intermediate Similarity	NPC475098
0.7396	Intermediate Similarity	NPC248775
0.7395	Intermediate Similarity	NPC471082

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 NPC197736 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1412
0.2-0.3	3706
0.3-0.4	2530
0.4-0.5	986
0.5-0.6	265
0.6-0.7	46
0.7-0.8	13
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD7838	Discovery
0.7759	Intermediate Similarity	NPD7503	Approved
0.7607	Intermediate Similarity	NPD8513	Phase 3
0.7589	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6686	Approved
0.7458	Intermediate Similarity	NPD8517	Approved
0.7458	Intermediate Similarity	NPD8516	Approved
0.7458	Intermediate Similarity	NPD8515	Approved
0.7379	Intermediate Similarity	NPD46	Approved
0.7379	Intermediate Similarity	NPD6698	Approved
0.7333	Intermediate Similarity	NPD7830	Approved
0.7333	Intermediate Similarity	NPD7829	Approved
0.7227	Intermediate Similarity	NPD8377	Approved
0.7227	Intermediate Similarity	NPD8294	Approved
0.7167	Intermediate Similarity	NPD8296	Approved
0.7167	Intermediate Similarity	NPD8033	Approved
0.7167	Intermediate Similarity	NPD8380	Approved
0.7167	Intermediate Similarity	NPD8335	Approved
0.7167	Intermediate Similarity	NPD8379	Approved
0.7167	Intermediate Similarity	NPD8378	Approved
0.6981	Remote Similarity	NPD7983	Approved
0.6917	Remote Similarity	NPD7328	Approved
0.6917	Remote Similarity	NPD7327	Approved
0.6885	Remote Similarity	NPD8444	Approved
0.688	Remote Similarity	NPD8448	Approved
0.686	Remote Similarity	NPD7516	Approved
0.685	Remote Similarity	NPD8390	Approved
0.685	Remote Similarity	NPD8391	Approved
0.685	Remote Similarity	NPD8392	Approved
0.68	Remote Similarity	NPD8451	Approved
0.6796	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5344	Discontinued
0.6723	Remote Similarity	NPD8133	Approved
0.6696	Remote Similarity	NPD6648	Approved
0.6639	Remote Similarity	NPD7641	Discontinued
0.6614	Remote Similarity	NPD8074	Phase 3
0.6587	Remote Similarity	NPD8342	Approved
0.6587	Remote Similarity	NPD8340	Approved
0.6587	Remote Similarity	NPD8299	Approved
0.6587	Remote Similarity	NPD8341	Approved
0.6577	Remote Similarity	NPD7839	Suspended
0.6535	Remote Similarity	NPD7507	Approved
0.6508	Remote Similarity	NPD7642	Approved
0.6508	Remote Similarity	NPD8328	Phase 3
0.6496	Remote Similarity	NPD6412	Phase 2
0.6385	Remote Similarity	NPD7319	Approved
0.6377	Remote Similarity	NPD7266	Discontinued
0.6356	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4251	Approved
0.6296	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6053	Discontinued
0.6204	Remote Similarity	NPD4249	Approved
0.6176	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4225	Approved
0.6172	Remote Similarity	NPD8080	Discontinued
0.6161	Remote Similarity	NPD5779	Approved
0.6161	Remote Similarity	NPD5778	Approved
0.616	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.616	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7154	Phase 3
0.6071	Remote Similarity	NPD7637	Suspended
0.6066	Remote Similarity	NPD6371	Approved
0.6036	Remote Similarity	NPD6101	Approved
0.6036	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7638	Approved
0.6032	Remote Similarity	NPD7115	Discovery
0.6032	Remote Similarity	NPD7505	Discontinued
0.5983	Remote Similarity	NPD7640	Approved
0.5983	Remote Similarity	NPD7639	Approved
0.5969	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD1407	Approved
0.5943	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.594	Remote Similarity	NPD7736	Approved
0.5929	Remote Similarity	NPD6411	Approved
0.5926	Remote Similarity	NPD7260	Phase 2
0.5909	Remote Similarity	NPD8273	Phase 1
0.5906	Remote Similarity	NPD7500	Approved
0.5887	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7524	Approved
0.585	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5785	Approved
0.584	Remote Similarity	NPD6429	Approved
0.584	Remote Similarity	NPD6430	Approved
0.5794	Remote Similarity	NPD4819	Approved
0.5794	Remote Similarity	NPD4822	Approved
0.5794	Remote Similarity	NPD4821	Approved
0.5794	Remote Similarity	NPD4820	Approved
0.578	Remote Similarity	NPD6110	Phase 1
0.5769	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD4271	Approved
0.5755	Remote Similarity	NPD4268	Approved
0.5752	Remote Similarity	NPD8455	Phase 2
0.5729	Remote Similarity	NPD6123	Approved
0.5727	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD969	Suspended
0.569	Remote Similarity	NPD5282	Discontinued
0.5685	Remote Similarity	NPD7625	Phase 1
0.5683	Remote Similarity	NPD8415	Approved
0.5682	Remote Similarity	NPD5126	Approved
0.5682	Remote Similarity	NPD6370	Approved
0.5682	Remote Similarity	NPD5125	Phase 3
0.5676	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5363	Approved
0.5676	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6695	Phase 3
0.563	Remote Similarity	NPD8293	Discontinued
0.5619	Remote Similarity	NPD8039	Approved
0.5612	Remote Similarity	NPD8450	Suspended
0.561	Remote Similarity	NPD4211	Phase 1
0.5606	Remote Similarity	NPD8269	Approved
0.5606	Remote Similarity	NPD8267	Approved
0.5606	Remote Similarity	NPD8268	Approved
0.5606	Remote Similarity	NPD8266	Approved
0.5603	Remote Similarity	NPD8171	Discontinued

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