NPASS Compound

Structure

NPC479376 OpenBabel06302215222D 86 93 0 0 0 0 0 0 0 0999 V2000 -13.5000 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0000 2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0000 2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5000 3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0000 4.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0000 4.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5000 3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5000 3.3301 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.0000 2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5000 1.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0000 2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5000 3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5000 3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0000 2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5000 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0000 0.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.0000 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 1.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 -0.1340 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5000 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0000 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0000 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -1.8660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -4.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -4.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.7321 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 1.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 0.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -2.7321 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5000 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5000 5.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0000 5.9282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.5000 5.0622 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -17.0000 4.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.5000 3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.0000 2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.0000 2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.5000 3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.5000 3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.0000 4.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.5000 5.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.5000 5.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.0000 4.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.0000 5.9282 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -17.1340 5.4282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.5000 6.7942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -18.8660 6.4282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -21.0000 4.1962 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -21.0000 5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -22.0000 4.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -21.0000 3.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -18.5000 1.5981 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -19.3660 2.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -19.0000 0.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.6340 1.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 7 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 62 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 11 61 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 15 61 1 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 19 20 2 0 0 0 0 20 25 1 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 28 29 2 0 0 0 0 29 34 1 0 0 0 0 29 30 1 0 0 0 0 30 31 2 0 0 0 0 31 32 1 0 0 0 0 31 36 1 0 0 0 0 32 33 1 0 0 0 0 33 34 2 0 0 0 0 34 35 1 0 0 0 0 36 37 2 0 0 0 0 36 38 1 0 0 0 0 38 39 2 0 0 0 0 39 48 1 0 0 0 0 39 40 1 0 0 0 0 40 41 1 0 0 0 0 41 42 2 0 0 0 0 42 43 1 0 0 0 0 42 57 1 0 0 0 0 43 48 2 0 0 0 0 43 44 1 0 0 0 0 44 45 2 0 0 0 0 45 46 1 0 0 0 0 45 53 1 0 0 0 0 46 47 2 0 0 0 0 47 48 1 0 0 0 0 47 49 1 0 0 0 0 49 50 2 0 0 0 0 49 51 2 0 0 0 0 49 52 1 0 0 0 0 53 54 2 0 0 0 0 53 55 2 0 0 0 0 53 56 1 0 0 0 0 57 58 2 0 0 0 0 57 59 2 0 0 0 0 57 60 1 0 0 0 0 62 63 2 0 0 0 0 62 64 1 0 0 0 0 64 65 2 0 0 0 0 65 74 1 0 0 0 0 65 66 1 0 0 0 0 66 67 1 0 0 0 0 67 68 2 0 0 0 0 68 69 1 0 0 0 0 68 83 1 0 0 0 0 69 74 2 0 0 0 0 69 70 1 0 0 0 0 70 71 2 0 0 0 0 71 72 1 0 0 0 0 71 79 1 0 0 0 0 72 73 2 0 0 0 0 73 74 1 0 0 0 0 73 75 1 0 0 0 0 75 76 2 0 0 0 0 75 77 2 0 0 0 0 75 78 1 0 0 0 0 79 80 2 0 0 0 0 79 81 2 0 0 0 0 79 82 1 0 0 0 0 83 84 2 0 0 0 0 83 85 2 0 0 0 0 83 86 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	222.2
Volume:	257.037
LogP:	4.007
LogD:	3.58
LogS:	-3.412
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.667
Synthetic Accessibility Score:	4.116
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.601
MDCK Permeability:	1.6013029380701482e-05
Pgp-inhibitor:	0.598
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.731
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211
Plasma Protein Binding (PPB):	92.73270416259766%
Volume Distribution (VD):	2.253
Pgp-substrate:	3.425550937652588%

ADMET: Metabolism

CYP1A2-inhibitor:	0.131
CYP1A2-substrate:	0.579
CYP2C19-inhibitor:	0.326
CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.81
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.122
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	7.478
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.615
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.141
Skin Sensitization:	0.255
Carcinogencity:	0.771
Eye Corrosion:	0.055
Eye Irritation:	0.494
Respiratory Toxicity:	0.097

Download Data

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

Natural Product: NPC479376

Natural Product ID:	NPC479376
*Common Name:**	VTCUUTNDNRAQSK-NCNWUEASSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VTCUUTNDNRAQSK-NCNWUEASSA-N
Standard InCHI:	InChI=1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-11,15-16,20-24H,12-14,17-19H2,1-2H3,(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80)/b52-31+,53-32+,54-37+,55-38+,56-39-,57-40-
SMILES:	CC1=CC=C(C/C/1=N/C(=O)C1=CC=C/C(=NC(=O)/N=C/2C=CC=C(C2)C(=O)/N=C2/C=C(CC=C2C)C(=O)/N=C/2CC=C(c3cc(cc(c23)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)/C1)C(=O)/N=C/1CC=C(c2cc(cc(c12)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO1276	Thonningia sanguinea	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843586]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18288807]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26539973]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27359053]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28294609]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28541699]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29019684]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29667822]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29878768]
NPO1276	Thonningia sanguinea	Species	Balanophoraceae	Eukaryota	Subaerial Parts	n.a.	n.a.	PMID[30207720]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32040324]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32173199]
NPO40759	Okeania sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32267694]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1276	Thonningia sanguinea	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	17
GI50	4
IC50	93
Kd	3
Ki	8
Others	33

Activity Type	# Activity
Cell Line	13
CELL-LINE	2
Individual Protein	62
NON-MOLECULAR	6
Organism	34
Others	11
PROTEIN COMPLEX	18
SINGLE PROTEIN	21

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	64.3	%	PMID[26965864]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	51.9	%	PMID[27014922]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	57.6	%	PMID[27014922]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	Ki	=	260.0	nM	PMID[27265686]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	Inhibition	=	79.0	%	PMID[28216402]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	Inhibition	=	31.0	%	PMID[28415012]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	Inhibition	=	73.0	%	PMID[28415012]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	IC50	=	14000.0	nM	PMID[28415012]
NPT612	Individual Protein	Canalicular multispecific organic anion transporter 1	Homo sapiens	IC50	=	36800.0	nM	PMID[23956101]
NPT1249	Individual Protein	Canalicular multispecific organic anion transporter 2	Homo sapiens	IC50	>	133000.0	nM	PMID[23956101]
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	IC50	>	133000.0	nM	PMID[23956101]
NPT4542	Individual Protein	NAD-dependent deacetylase sirtuin 3	Homo sapiens	IC50	>	200000.0	nM	PMID[28475330]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	IC50	=	2800.0	nM	PMID[28475330]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	IC50	=	13000.0	nM	PMID[28475330]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	Inhibition	=	79.0	%	PMID[28756024]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	IC50	=	8670.0	nM	PMID[28735213]
NPT4507	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 3	Homo sapiens	IC50	=	1270.0	nM	PMID[28735213]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	2900.0	nM	PMID[29878768]
NPT2674	Individual Protein	P2X purinoceptor 1	Homo sapiens	IC50	=	4300.0	nM	PMID[29649742]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	100000.0	nM	PMID[29885575]
NPT3012	Individual Protein	Heparanase	Homo sapiens	IC50	=	26600.0	nM	PMID[28811133]
NPT5846	Individual Protein	Putative silent information regulator 2	Leishmania infantum	IC50	=	7000.0	nM	PMID[28241112]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	1420.0	nM	PMID[30207720]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	Ki	=	260.0	nM	PMID[30108800]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	Ki	=	780.0	nM	PMID[30108800]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	Ki	=	1070.0	nM	PMID[30108800]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	Ki	=	1030.0	nM	PMID[30108800]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	IC50	=	8670.0	nM	PMID[30108800]
NPT4507	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 3	Homo sapiens	IC50	=	1270.0	nM	PMID[30015078]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	IC50	=	8670.0	nM	PMID[30015078]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	100000.0	nM	PMID[30092366]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	IC50	=	8670.0	nM	PMID[31382118]
NPT4507	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 3	Homo sapiens	IC50	=	1270.0	nM	PMID[31382118]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	IC50	=	8670.0	nM	PMID[31088715]
NPT4507	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 3	Homo sapiens	IC50	=	1270.0	nM	PMID[31088715]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	100000.0	nM	PMID[32292551]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	>	100000.0	nM	PMID[30986574]
NPT189	Cell Line	Vero	Chlorocebus aethiops	TC50	>	200.0	uM	PMID[30925051]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	IC50	=	6700.0	nM	PMID[31223439]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	IC50	=	17000.0	nM	PMID[31223439]
NPT171	Cell Line	MRC5	Homo sapiens	EC50	>	64000.0	nM	PMID[30677668]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	IC50	=	5000.0	nM	PMID[27687971]
NPT4907	Individual Protein	Tyrosyl-DNA phosphodiesterase 2	Homo sapiens	EC50	=	24000.0	nM	PMID[27687971]
NPT2674	Individual Protein	P2X purinoceptor 1	Homo sapiens	IC50	=	4270.0	nM	PMID[27427902]
NPT2669	Individual Protein	P2X purinoceptor 1	Rattus norvegicus	IC50	=	4680.0	nM	PMID[27427902]
NPT2669	Individual Protein	P2X purinoceptor 1	Rattus norvegicus	IC50	=	1000.0	nM	PMID[32345019]
NPT2674	Individual Protein	P2X purinoceptor 1	Homo sapiens	Inhibition	>	90.0	%	PMID[32345019]
NPT2674	Individual Protein	P2X purinoceptor 1	Homo sapiens	Inhibition	>	40.0	%	PMID[32345019]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>=	10000.0	nM	PMID[32008883]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	IC50	=	27.0	nM	PMID[32163813]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	IC50	=	35.0	nM	PMID[32163813]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	IC50	=	2200.0	nM	PMID[32163813]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	IC50	=	23300.0	nM	PMID[32163813]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	Inhibition	=	94.52	%	PMID[33360574]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	Inhibition	=	98.37	%	PMID[33360574]
NPT4542	Individual Protein	NAD-dependent deacetylase sirtuin 3	Homo sapiens	Inhibition	=	96.82	%	PMID[33360574]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	154000.0	nM	PMID[32827875]
NPT4503	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Homo sapiens	IC50	=	7770.0	nM	PMID[32883636]
NPT4507	Individual Protein	Ectonucleotide pyrophosphatase/phosphodiesterase family member 3	Homo sapiens	IC50	=	890.0	nM	PMID[32883636]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	67400.0	nM	PMID[32631535]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	>	100000.0	nM	PMID[33071053]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	100000.0	nM	PMID[32652409]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	100000.0	nM	PMID[32795774]
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	Inhibition	=	95.0	%	PMID[32858418]
NPT1158	Individual Protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	Inhibition	=	72.0	%	PMID[32858418]
NPT4542	Individual Protein	NAD-dependent deacetylase sirtuin 3	Homo sapiens	Inhibition	=	10.0	%	PMID[32858418]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	20.0	nM	PMID[26922226]
NPT23878	SINGLE PROTEIN	Translin-associated protein X	Homo sapiens	Inhibition	=	61.0	%	PMID[27641467]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	38.0	nM	PMID[27155468]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	IC50	=	7900.0	nM	PMID[27720295]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	IC50	>	250000.0	nM	PMID[27720295]
NPT21774	PROTEIN COMPLEX	HSP60/HSP10	Homo sapiens	IC50	=	11000.0	nM	PMID[27720295]
NPT21774	PROTEIN COMPLEX	HSP60/HSP10	Homo sapiens	IC50	>	250000.0	nM	PMID[27720295]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	120.0	nM	PMID[27720295]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	100000.0	nM	PMID[27720295]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	63000.0	nM	PMID[27720295]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1200.0	nM	PMID[27359053]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	>	135000.0	nM	PMID[20829430]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	107000.0	nM	PMID[22961681]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	38.0	nM	PMID[29323491]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	>	133000.0	nM	PMID[23956101]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	46.0	nM	PMID[29590751]
NPT20950	CELL-LINE	Erythrocyte	n.a.	IC50	=	120000.0	nM	PMID[29631958]
NPT20950	CELL-LINE	Erythrocyte	n.a.	IC50	=	180000.0	nM	PMID[29631958]
NPT19119	SINGLE PROTEIN	Chromobox protein homolog 7	Homo sapiens	IC50	=	8100.0	nM	PMID[28478342]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	20.0	nM	PMID[29197735]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	20.0	nM	PMID[29197735]
NPT2	Others	Unspecified		IC50	>	64000.0	nM	PMID[29197735]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	Activity	=	100.0	%	PMID[29197735]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	20.0	nM	PMID[29885575]
NPT19120	SINGLE PROTEIN	Heparanase	Mus musculus	Ki	=	48000.0	nM	PMID[28811133]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	IC50	=	39.81	nM	PMID[29672041]
NPT19122	SINGLE PROTEIN	Subtilisin/kexin type 9	Homo sapiens	FC	=	15.0	n.a.	PMID[29519739]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	IC50	=	4.0	nM	PMID[29609908]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	30.0	nM	PMID[29604541]
NPT2	Others	Unspecified		Ratio	=	76.0	n.a.	PMID[29604541]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	IC50	=	180.0	nM	PMID[30100019]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	199.53	nM	PMID[29107420]
NPT19123	SINGLE PROTEIN	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Rattus norvegicus	IC50	=	72000.0	nM	PMID[30108800]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	40.0	nM	PMID[30344906]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	30.0	nM	PMID[30092366]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	3333.0	n.a.	PMID[30092366]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	5.0	nM	PMID[31732256]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	IC50	=	20.0	nM	PMID[30638761]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	30.0	nM	PMID[30638761]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	30.0	nM	PMID[32292551]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	3333.0	n.a.	PMID[32292551]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	GI50	=	32.0	nM	PMID[30986574]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	IC50	=	39.81	nM	PMID[31378593]
NPT2	Others	Unspecified		IC50	=	240.0	nM	PMID[31841625]
NPT19122	SINGLE PROTEIN	Subtilisin/kexin type 9	Homo sapiens	Kd	=	190000.0	nM	PMID[30448414]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	30.0	nM	PMID[30655943]
NPT22368	ORGANISM	Zika virus	Zika virus	IC50	=	44020.0	nM	PMID[30925051]
NPT21773	SINGLE PROTEIN	Thiosulfate sulfurtransferase	Homo sapiens	IC50	>	100000.0	nM	PMID[30852084]
NPT2	Others	Unspecified		IC50	>	63000.0	nM	PMID[30852084]
NPT21775	SINGLE PROTEIN	60 kDa chaperonin	Escherichia coli (strain K12)	Kd	=	9800.0	nM	PMID[30852084]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	IC50	=	16000.0	nM	PMID[30852084]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	IC50	=	8100.0	nM	PMID[30852084]
NPT21774	PROTEIN COMPLEX	HSP60/HSP10	Homo sapiens	IC50	=	7200.0	nM	PMID[30852084]
NPT21775	SINGLE PROTEIN	60 kDa chaperonin	Escherichia coli (strain K12)	IC50	>	250000.0	nM	PMID[30852084]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	20.0	%	PMID[30852084]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	42.0	%	PMID[30852084]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	50.0	nM	PMID[30677668]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	EC50	=	40.0	nM	PMID[30677668]
NPT2	Others	Unspecified		Ratio EC50	>	1280.0	n.a.	PMID[30677668]
NPT2	Others	Unspecified		Ratio EC50	>	1600.0	n.a.	PMID[30677668]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	Ki	=	750.0	nM	PMID[26771861]
NPT194	Organism	Dengue virus 2	Dengue virus 2	EC50	=	40000.0	nM	PMID[26771861]
NPT22367	SINGLE PROTEIN	Genome polyprotein	Zika virus	IC50	=	47000.0	nM	PMID[31980339]
NPT22367	SINGLE PROTEIN	Genome polyprotein	Zika virus	EC50	=	1930.0	nM	PMID[31980339]
NPT22367	SINGLE PROTEIN	Genome polyprotein	Zika virus	Kd	=	28000.0	nM	PMID[31980339]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	EC50	=	4.0	nM	PMID[32527539]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	28.0	nM	PMID[31931339]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	EC50	=	33.0	nM	PMID[31931339]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	78.0	nM	PMID[31978782]
NPT707	Individual Protein	NAD-dependent protein deacylase sirtuin-5, mitochondrial	Homo sapiens	IC50	=	11000.0	nM	PMID[32163813]
NPT707	Individual Protein	NAD-dependent protein deacylase sirtuin-5, mitochondrial	Homo sapiens	IC50	=	2730.0	nM	PMID[32163813]
NPT2	Others	Unspecified		IC50	=	25.0	nM	PMID[32294613]
NPT2	Others	Unspecified		IC50	=	70.0	nM	PMID[32294613]
NPT26739	SINGLE PROTEIN	Ectonucleoside triphosphate diphosphohydrolase 1	Mus musculus	IC50	>	100000.0	nM	PMID[32786396]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	30.0	nM	PMID[33385837]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	40.0	nM	PMID[33385837]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	GI50	=	58.0	nM	PMID[33071053]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	30.0	nM	PMID[32652409]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	30.0	nM	PMID[32795774]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	3333.0	n.a.	PMID[32795774]
NPT707	Individual Protein	NAD-dependent protein deacylase sirtuin-5, mitochondrial	Homo sapiens	Inhibition	=	53.0	%	PMID[32858418]
NPT28021	SINGLE PROTEIN	Ectonucleoside triphosphate diphosphohydrolase 1	Homo sapiens	IC50	=	16100.0	nM	PMID[28735213]
NPT28022	SINGLE PROTEIN	Ectonucleoside triphosphate diphosphohydrolase 2	Homo sapiens	IC50	=	24100.0	nM	PMID[28735213]
NPT28023	SINGLE PROTEIN	Ectonucleoside triphosphate diphosphohydrolase 3	Homo sapiens	IC50	=	4310.0	nM	PMID[28735213]
NPT28024	SINGLE PROTEIN	Ectonucleoside triphosphate diphosphohydrolase 8	Homo sapiens	IC50	>	100000.0	nM	PMID[28735213]
NPT28021	SINGLE PROTEIN	Ectonucleoside triphosphate diphosphohydrolase 1	Homo sapiens	IC50	=	16000.0	nM	PMID[32786396]
NPT28022	SINGLE PROTEIN	Ectonucleoside triphosphate diphosphohydrolase 2	Homo sapiens	IC50	=	24000.0	nM	PMID[32786396]
NPT28023	SINGLE PROTEIN	Ectonucleoside triphosphate diphosphohydrolase 3	Homo sapiens	IC50	=	4300.0	nM	PMID[32786396]
NPT28024	SINGLE PROTEIN	Ectonucleoside triphosphate diphosphohydrolase 8	Homo sapiens	IC50	>	100000.0	nM	PMID[32786396]

☑ 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 NPC479376 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	284
0.1-0.2	2787
0.2-0.3	12621
0.3-0.4	22700
0.4-0.5	4084
0.5-0.6	218
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID

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 NPC479376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	909
0.2-0.3	1127
0.3-0.4	4294
0.4-0.5	2427
0.5-0.6	213
0.6-0.7	9
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

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