NPASS Compound

Structure

CID49195 OpenBabel06191715382D 83 91 0 0 1 0 0 0 0 0999 V2000 -4.3908 11.1305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0778 -4.1081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3721 -4.4089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8587 9.8450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3623 5.1726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7931 -0.0282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5645 10.1457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5970 2.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9481 6.1727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6573 2.8347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7706 1.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7744 7.1575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1820 5.5299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9738 -1.2922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0339 9.4427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2580 2.2362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8912 2.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0046 0.8651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8347 7.4996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2423 5.8720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0282 -1.6178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0523 9.2519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6019 1.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5187 8.5680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9563 -0.2924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7430 3.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2988 0.5643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1290 7.1988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0061 -2.5225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7552 3.3665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1434 6.7650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1381 -3.7661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7984 9.5029 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4226 4.8305 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7931 -1.0282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0649 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0687 6.8568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3591 0.9063 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3630 6.5560 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2807 7.2631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6180 3.8646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5736 -0.8192 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9304 8.2593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6814 1.8722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9721 -2.7813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9645 -2.7813 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9721 8.5181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6558 -1.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5736 6.5560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3591 4.8305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2807 -1.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9645 8.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3630 -0.8192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6180 1.8722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0061 8.2593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9304 -2.5225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6814 3.8646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6558 7.2631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4226 0.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0998 -2.0998 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.7369 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.9365 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.9365 5.7369 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.7051 2.8684 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0998 7.8367 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9683 -2.8684 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9683 8.6053 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.8367 -2.0998 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.8367 7.8367 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 0.7686 2.8684 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7984 -3.7661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1925 7.1988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2988 5.1726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6379 -2.2923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1381 9.5029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1290 -1.4619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6662 4.0383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2986 8.0292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3623 0.5643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7552 2.3703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0061 7.2631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9304 -1.5263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 32 1 0 0 0 0 3 32 1 0 0 0 0 6 35 1 0 0 0 0 7 33 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 21 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 16 26 1 0 0 0 0 17 36 2 0 0 0 0 18 36 1 0 0 0 0 19 37 2 0 0 0 0 20 37 1 0 0 0 0 24 69 1 0 0 0 0 25 70 1 0 0 0 0 26 71 1 0 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 29 45 1 0 0 0 0 29 60 1 0 0 0 0 30 41 2 0 0 0 0 30 81 1 0 0 0 0 31 40 2 0 0 0 0 31 82 1 0 0 0 0 33 4 1 6 0 0 0 34 5 1 1 0 0 0 34 57 1 0 0 0 0 34 61 1 0 0 0 0 35 48 2 0 0 0 0 35 83 1 0 0 0 0 38 27 1 1 0 0 0 38 54 1 0 0 0 0 38 62 1 0 0 0 0 39 28 1 1 0 0 0 39 58 1 0 0 0 0 39 63 1 0 0 0 0 40 49 1 0 0 0 0 40 65 1 0 0 0 0 41 50 1 0 0 0 0 41 64 1 0 0 0 0 42 21 1 1 0 0 0 42 51 1 0 0 0 0 42 70 1 0 0 0 0 43 22 1 1 0 0 0 43 52 1 0 0 0 0 43 69 1 0 0 0 0 44 23 1 1 0 0 0 44 59 1 0 0 0 0 44 71 1 0 0 0 0 45 66 2 3 0 0 0 45 72 1 0 0 0 0 46 32 1 1 0 0 0 46 56 1 0 0 0 0 46 66 1 0 0 0 0 47 33 1 1 0 0 0 47 55 1 0 0 0 0 47 67 1 0 0 0 0 48 53 1 0 0 0 0 48 68 1 0 0 0 0 49 61 2 3 0 0 0 49 73 1 0 0 0 0 50 63 2 3 0 0 0 50 74 1 0 0 0 0 51 60 2 3 0 0 0 51 75 1 0 0 0 0 52 67 2 3 0 0 0 52 76 1 0 0 0 0 53 62 2 3 0 0 0 53 77 1 0 0 0 0 54 64 2 0 0 0 0 54 81 1 0 0 0 0 55 65 2 0 0 0 0 55 82 1 0 0 0 0 56 68 2 0 0 0 0 56 83 1 0 0 0 0 57 71 1 0 0 0 0 57 78 2 0 0 0 0 58 69 1 0 0 0 0 58 79 2 0 0 0 0 59 70 1 0 0 0 0 59 80 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1140.54
Volume:	1134.09
LogP:	5.49
LogD:	3.614
LogS:	-3.229
# Rotatable Bonds:	7
TPSA:	320.6
# H-Bond Aceptor:	24
# H-Bond Donor:	6
# Rings:	9
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.119
Synthetic Accessibility Score:	4.207
Fsp3:	0.492
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.257
MDCK Permeability:	4.656435976357898e-06
Pgp-inhibitor:	0.082
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	88.78082275390625%
Volume Distribution (VD):	4.776
Pgp-substrate:	5.593203544616699%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.599
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.461
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	4.809
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.995
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.762
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.036
Carcinogencity:	0.357
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC49195

Natural Product ID:	NPC49195
*Common Name:**	Wewakazole
IUPAC Name:	n.a.
Synonyms:	Wewakazole
Standard InCHIKey:	LRFQMOZAQWOOPZ-IBFZZIGPSA-N
Standard InCHI:	InChI=1S/C59H72N12O12/c1-7-33(4)47-55-65-40(31-82-55)49(73)61-34(5)57(78)71-26-16-23-44(71)59(80)70-25-14-21-42(70)51(75)60-29-45(72)66-46(32(2)3)56-68-48(35(6)83-56)53(77)62-38(27-36-17-10-8-11-18-36)54-64-41(30-81-54)50(74)63-39(28-37-19-12-9-13-20-37)58(79)69-24-15-22-43(69)52(76)67-47/h8-13,17-20,30-34,38-39,42-44,46-47H,7,14-16,21-29H2,1-6H3,(H,60,75)(H,61,73)(H,62,77)(H,63,74)(H,66,72)(H,67,76)/t33-,34-,38-,39-,42-,43-,44-,46-,47-/m0/s1
SMILES:	CC[C@@H]([C@@H]1N=C(O)[C@@H]2CCCN2C(=O)[C@H](Cc2ccccc2)N=C(O)c2coc(n2)[C@H](Cc2ccccc2)N=C(O)c2nc(oc2C)[C@@H](N=C(CN=C([C@H]2N(C(=O)[C@H]3N(C(=O)[C@@H](N=C(c4nc1oc4)O)C)CCC3)CCC2)O)O)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669190
PubChem CID:	21578002
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
NPO30527	Lyngbya	Genus	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14695793]
NPO30527	Lyngbya	Genus	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18693761]
NPO30527	Lyngbya	Genus	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21155594]
NPO30527	Lyngbya	Genus	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21650153]
NPO30527	Lyngbya	Genus	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24111939]
NPO40567	Moorea producens	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26980238]
NPO40567	Moorea producens	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28448144]
NPO40567	Moorea producens	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28535042]
NPO40567	Moorea producens	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31468974]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	10100.0	nM	PMID[480951]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	10000.0	nM	PMID[480952]

☑ 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 NPC49195 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	348
0.1-0.2	2193
0.2-0.3	13576
0.3-0.4	12977
0.4-0.5	10362
0.5-0.6	2859
0.6-0.7	371
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.7191	Intermediate Similarity	NPC477590
0.7191	Intermediate Similarity	NPC477588
0.7191	Intermediate Similarity	NPC477586
0.7191	Intermediate Similarity	NPC477585
0.7106	Intermediate Similarity	NPC477587
0.7106	Intermediate Similarity	NPC477589
0.7038	Intermediate Similarity	NPC315061
0.7027	Intermediate Similarity	NPC315411
0.6974	Remote Similarity	NPC315804
0.6974	Remote Similarity	NPC313804
0.691	Remote Similarity	NPC186351
0.6897	Remote Similarity	NPC476830
0.6863	Remote Similarity	NPC141957
0.6863	Remote Similarity	NPC302597
0.686	Remote Similarity	NPC136797
0.6853	Remote Similarity	NPC476826
0.6853	Remote Similarity	NPC476831
0.6853	Remote Similarity	NPC476827
0.6838	Remote Similarity	NPC325683
0.6824	Remote Similarity	NPC477219
0.68	Remote Similarity	NPC162860
0.6795	Remote Similarity	NPC37924
0.6792	Remote Similarity	NPC478029
0.6786	Remote Similarity	NPC54420
0.6766	Remote Similarity	NPC476828
0.6765	Remote Similarity	NPC220852
0.675	Remote Similarity	NPC285343
0.6723	Remote Similarity	NPC168135
0.6723	Remote Similarity	NPC477218
0.6723	Remote Similarity	NPC322800
0.6708	Remote Similarity	NPC478028
0.6682	Remote Similarity	NPC96016
0.6681	Remote Similarity	NPC299035
0.6681	Remote Similarity	NPC177432
0.6667	Remote Similarity	NPC476829
0.6652	Remote Similarity	NPC107077
0.6652	Remote Similarity	NPC223791
0.6598	Remote Similarity	NPC325976
0.6587	Remote Similarity	NPC469904
0.6579	Remote Similarity	NPC478158
0.657	Remote Similarity	NPC254700
0.6564	Remote Similarity	NPC316403
0.6548	Remote Similarity	NPC316008
0.6548	Remote Similarity	NPC313867
0.654	Remote Similarity	NPC477462
0.6537	Remote Similarity	NPC473003
0.6524	Remote Similarity	NPC238945
0.6515	Remote Similarity	NPC314358
0.6509	Remote Similarity	NPC478157
0.6505	Remote Similarity	NPC241794
0.6497	Remote Similarity	NPC314388
0.6497	Remote Similarity	NPC315283
0.6494	Remote Similarity	NPC251036
0.6485	Remote Similarity	NPC261934
0.6485	Remote Similarity	NPC202198
0.6485	Remote Similarity	NPC476832
0.6485	Remote Similarity	NPC5194
0.6475	Remote Similarity	NPC28945
0.6462	Remote Similarity	NPC279871
0.6462	Remote Similarity	NPC26108
0.6458	Remote Similarity	NPC194740
0.6456	Remote Similarity	NPC469902
0.6453	Remote Similarity	NPC473002
0.6449	Remote Similarity	NPC474183
0.6442	Remote Similarity	NPC472923
0.6435	Remote Similarity	NPC167763
0.6435	Remote Similarity	NPC470903
0.6435	Remote Similarity	NPC470112
0.6432	Remote Similarity	NPC326363
0.6429	Remote Similarity	NPC171317
0.6426	Remote Similarity	NPC281049
0.6426	Remote Similarity	NPC303658
0.6415	Remote Similarity	NPC137627
0.6411	Remote Similarity	NPC75179
0.6408	Remote Similarity	NPC184680
0.6406	Remote Similarity	NPC294951
0.6405	Remote Similarity	NPC14288
0.6404	Remote Similarity	NPC262166
0.6389	Remote Similarity	NPC316110
0.6389	Remote Similarity	NPC315893
0.6389	Remote Similarity	NPC313587
0.6382	Remote Similarity	NPC470784
0.6382	Remote Similarity	NPC470785
0.638	Remote Similarity	NPC117244
0.638	Remote Similarity	NPC473763
0.6379	Remote Similarity	NPC475196
0.6375	Remote Similarity	NPC319232
0.6375	Remote Similarity	NPC24370
0.6372	Remote Similarity	NPC269750
0.6372	Remote Similarity	NPC194671
0.6367	Remote Similarity	NPC315499
0.6364	Remote Similarity	NPC322135
0.6364	Remote Similarity	NPC145178
0.6364	Remote Similarity	NPC475350
0.6364	Remote Similarity	NPC14877
0.6356	Remote Similarity	NPC309919
0.6355	Remote Similarity	NPC469900
0.6352	Remote Similarity	NPC75634
0.6351	Remote Similarity	NPC165538
0.635	Remote Similarity	NPC262077
0.6349	Remote Similarity	NPC304307
0.6349	Remote Similarity	NPC118559
0.6349	Remote Similarity	NPC124920
0.6349	Remote Similarity	NPC34580
0.6349	Remote Similarity	NPC323244
0.6344	Remote Similarity	NPC475506
0.6339	Remote Similarity	NPC314882
0.6332	Remote Similarity	NPC476978
0.6329	Remote Similarity	NPC469898
0.6324	Remote Similarity	NPC14812
0.6322	Remote Similarity	NPC100547
0.6316	Remote Similarity	NPC155143
0.6311	Remote Similarity	NPC477516
0.6304	Remote Similarity	NPC478006
0.6304	Remote Similarity	NPC472286
0.6304	Remote Similarity	NPC472287
0.6301	Remote Similarity	NPC315542
0.6298	Remote Similarity	NPC314817
0.6298	Remote Similarity	NPC66191
0.6298	Remote Similarity	NPC316297
0.6296	Remote Similarity	NPC475421
0.6296	Remote Similarity	NPC223409
0.6296	Remote Similarity	NPC95240
0.6287	Remote Similarity	NPC314270
0.6286	Remote Similarity	NPC284888
0.6286	Remote Similarity	NPC323198
0.6286	Remote Similarity	NPC323752
0.6283	Remote Similarity	NPC472284
0.6283	Remote Similarity	NPC473640
0.6281	Remote Similarity	NPC261251
0.6276	Remote Similarity	NPC474896
0.6275	Remote Similarity	NPC233702
0.6269	Remote Similarity	NPC200589
0.6267	Remote Similarity	NPC472999
0.6262	Remote Similarity	NPC469903
0.6261	Remote Similarity	NPC163961
0.6261	Remote Similarity	NPC473305
0.6261	Remote Similarity	NPC122427
0.6261	Remote Similarity	NPC329961
0.6256	Remote Similarity	NPC295653
0.6256	Remote Similarity	NPC471050
0.6256	Remote Similarity	NPC471048
0.6256	Remote Similarity	NPC107458
0.6256	Remote Similarity	NPC471049
0.6255	Remote Similarity	NPC54744
0.625	Remote Similarity	NPC31097
0.625	Remote Similarity	NPC473001
0.6245	Remote Similarity	NPC102593
0.6245	Remote Similarity	NPC321592
0.6245	Remote Similarity	NPC54803
0.6245	Remote Similarity	NPC328924
0.6245	Remote Similarity	NPC196718
0.6245	Remote Similarity	NPC89987
0.6244	Remote Similarity	NPC122590
0.624	Remote Similarity	NPC214142
0.6238	Remote Similarity	NPC471053
0.6238	Remote Similarity	NPC471052
0.6238	Remote Similarity	NPC471051
0.6238	Remote Similarity	NPC16188
0.6237	Remote Similarity	NPC130309
0.6225	Remote Similarity	NPC475168
0.6225	Remote Similarity	NPC473491
0.6225	Remote Similarity	NPC7817
0.6224	Remote Similarity	NPC205372
0.6217	Remote Similarity	NPC475774
0.6215	Remote Similarity	NPC316224
0.6211	Remote Similarity	NPC102008
0.621	Remote Similarity	NPC314523
0.621	Remote Similarity	NPC58001
0.6207	Remote Similarity	NPC240848
0.6206	Remote Similarity	NPC161801
0.62	Remote Similarity	NPC161069
0.6199	Remote Similarity	NPC276120
0.6197	Remote Similarity	NPC256912
0.6197	Remote Similarity	NPC30527
0.6194	Remote Similarity	NPC33064
0.6194	Remote Similarity	NPC245055
0.6193	Remote Similarity	NPC91179
0.619	Remote Similarity	NPC211555
0.6189	Remote Similarity	NPC33949
0.6186	Remote Similarity	NPC306804
0.6185	Remote Similarity	NPC314222
0.6185	Remote Similarity	NPC196449
0.6183	Remote Similarity	NPC478141
0.6176	Remote Similarity	NPC305984
0.6173	Remote Similarity	NPC287401
0.6169	Remote Similarity	NPC140284
0.6169	Remote Similarity	NPC75609
0.6168	Remote Similarity	NPC475123
0.6168	Remote Similarity	NPC475204
0.6167	Remote Similarity	NPC272174
0.6166	Remote Similarity	NPC72715
0.616	Remote Similarity	NPC315467
0.6157	Remote Similarity	NPC159767
0.6157	Remote Similarity	NPC155506
0.6157	Remote Similarity	NPC208297
0.6157	Remote Similarity	NPC165964
0.6157	Remote Similarity	NPC314633
0.6157	Remote Similarity	NPC224395
0.6157	Remote Similarity	NPC164608

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 NPC49195 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	586
0.2-0.3	967
0.3-0.4	2025
0.4-0.5	3935
0.5-0.6	1358
0.6-0.7	68
0.7-0.8	3
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
0.7644	Intermediate Similarity	NPD7490	Discontinued
0.7596	Intermediate Similarity	NPD6347	Phase 2
0.7005	Intermediate Similarity	NPD6857	Phase 3
0.6957	Remote Similarity	NPD8356	Approved
0.691	Remote Similarity	NPD8430	Approved
0.687	Remote Similarity	NPD7180	Phase 3
0.6826	Remote Similarity	NPD6974	Phase 3
0.6781	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6169	Phase 1
0.6667	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7031	Phase 1
0.6639	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7853	Phase 2
0.6564	Remote Similarity	NPD8322	Phase 2
0.6544	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD3945	Discontinued
0.6516	Remote Similarity	NPD7944	Discontinued
0.6509	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8247	Approved
0.6508	Remote Similarity	NPD8246	Approved
0.6478	Remote Similarity	NPD3392	Approved
0.6471	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD2951	Discontinued
0.646	Remote Similarity	NPD2779	Approved
0.6453	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5924	Discontinued
0.6432	Remote Similarity	NPD5479	Discontinued
0.6426	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7470	Discontinued
0.6376	Remote Similarity	NPD7001	Phase 3
0.6352	Remote Similarity	NPD5866	Approved
0.6341	Remote Similarity	NPD4368	Phase 2
0.6332	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD2778	Approved
0.6324	Remote Similarity	NPD7131	Phase 3
0.6303	Remote Similarity	NPD5850	Phase 3
0.63	Remote Similarity	NPD7896	Approved
0.6275	Remote Similarity	NPD5532	Phase 2
0.6275	Remote Similarity	NPD8463	Approved
0.627	Remote Similarity	NPD1867	Approved
0.6266	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7483	Phase 2
0.6256	Remote Similarity	NPD7482	Phase 2
0.625	Remote Similarity	NPD5922	Phase 3
0.6244	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.624	Remote Similarity	NPD8116	Phase 3
0.624	Remote Similarity	NPD7022	Phase 2
0.624	Remote Similarity	NPD7603	Discontinued
0.624	Remote Similarity	NPD3263	Phase 3
0.624	Remote Similarity	NPD8117	Approved
0.623	Remote Similarity	NPD5817	Discontinued
0.623	Remote Similarity	NPD1659	Phase 1
0.6226	Remote Similarity	NPD8255	Phase 2
0.6225	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD8016	Phase 3
0.622	Remote Similarity	NPD6475	Phase 2
0.6213	Remote Similarity	NPD8525	Approved
0.6211	Remote Similarity	NPD7777	Approved
0.6211	Remote Similarity	NPD7778	Approved
0.6211	Remote Similarity	NPD53	Approved
0.6204	Remote Similarity	NPD8349	Phase 1
0.6202	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD3875	Discontinued
0.619	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD8324	Phase 2
0.6178	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5640	Discontinued
0.6165	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD8173	Phase 2
0.6162	Remote Similarity	NPD8172	Phase 2
0.616	Remote Similarity	NPD1638	Discovery
0.6154	Remote Similarity	NPD7952	Approved
0.6154	Remote Similarity	NPD7790	Approved
0.6154	Remote Similarity	NPD7789	Approved
0.6154	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7791	Approved
0.6154	Remote Similarity	NPD7953	Approved
0.6154	Remote Similarity	NPD7950	Approved
0.6154	Remote Similarity	NPD7951	Approved
0.6151	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.615	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6137	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7921	Approved
0.6122	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7781	Approved
0.6122	Remote Similarity	NPD8104	Phase 3
0.6122	Remote Similarity	NPD8284	Discontinued
0.6122	Remote Similarity	NPD7780	Approved
0.6116	Remote Similarity	NPD6209	Approved
0.6111	Remote Similarity	NPD6716	Phase 1
0.6111	Remote Similarity	NPD7665	Phase 2
0.6111	Remote Similarity	NPD4322	Discontinued
0.6111	Remote Similarity	NPD7666	Phase 3
0.6102	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD8359	Phase 2
0.61	Remote Similarity	NPD8479	Phase 2
0.6099	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD3507	Phase 2
0.6094	Remote Similarity	NPD4130	Phase 3
0.6094	Remote Similarity	NPD8403	Phase 1
0.6083	Remote Similarity	NPD6568	Discontinued
0.6082	Remote Similarity	NPD4086	Phase 1
0.6082	Remote Similarity	NPD7730	Approved
0.6082	Remote Similarity	NPD8292	Phase 2
0.6082	Remote Similarity	NPD7731	Approved
0.6068	Remote Similarity	NPD7222	Phase 2
0.6068	Remote Similarity	NPD7452	Approved
0.6068	Remote Similarity	NPD7453	Approved
0.6062	Remote Similarity	NPD6665	Discontinued
0.6061	Remote Similarity	NPD7817	Phase 1
0.6061	Remote Similarity	NPD6321	Discontinued
0.6059	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD5256	Discontinued
0.6053	Remote Similarity	NPD5512	Phase 3
0.6053	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7485	Phase 3
0.6047	Remote Similarity	NPD7484	Phase 3
0.6043	Remote Similarity	NPD6999	Discontinued
0.6043	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD8289	Discontinued
0.6041	Remote Similarity	NPD7426	Phase 1
0.6034	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7824	Approved
0.6031	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD7716	Approved
0.6025	Remote Similarity	NPD7717	Approved
0.6023	Remote Similarity	NPD8370	Discontinued
0.6018	Remote Similarity	NPD4204	Approved
0.6018	Remote Similarity	NPD4203	Approved
0.6015	Remote Similarity	NPD7924	Phase 2
0.6015	Remote Similarity	NPD7925	Phase 2
0.6008	Remote Similarity	NPD1505	Phase 2
0.6008	Remote Similarity	NPD4923	Phase 1
0.6008	Remote Similarity	NPD7688	Phase 1
0.6008	Remote Similarity	NPD1466	Phase 3
0.6008	Remote Similarity	NPD1467	Approved
0.6007	Remote Similarity	NPD8459	Approved
0.6007	Remote Similarity	NPD8460	Approved
0.6	Remote Similarity	NPD7271	Approved
0.6	Remote Similarity	NPD7967	Discontinued
0.6	Remote Similarity	NPD772	Phase 3
0.6	Remote Similarity	NPD4334	Discontinued
0.6	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7727	Phase 2
0.5991	Remote Similarity	NPD4372	Phase 1
0.5991	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD5857	Phase 3
0.5984	Remote Similarity	NPD4885	Approved
0.5984	Remote Similarity	NPD7797	Approved
0.5984	Remote Similarity	NPD7796	Approved
0.5983	Remote Similarity	NPD8115	Approved
0.5983	Remote Similarity	NPD8114	Approved
0.5983	Remote Similarity	NPD8098	Approved
0.5979	Remote Similarity	NPD8524	Approved
0.5975	Remote Similarity	NPD7467	Discontinued
0.5975	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD6452	Discontinued
0.5973	Remote Similarity	NPD5316	Approved
0.5973	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD8101	Phase 3
0.596	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.5958	Remote Similarity	NPD5293	Phase 2
0.5958	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5003	Discontinued
0.5951	Remote Similarity	NPD7994	Phase 2
0.595	Remote Similarity	NPD7878	Phase 2
0.595	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD8240	Discontinued
0.5941	Remote Similarity	NPD8096	Phase 3
0.5941	Remote Similarity	NPD8097	Phase 3
0.5938	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.593	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8271	Discontinued
0.5909	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD6376	Discontinued
0.5906	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD8063	Discontinued
0.5903	Remote Similarity	NPD3321	Discontinued
0.5902	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD5898	Approved
0.5901	Remote Similarity	NPD5899	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