NPASS Compound

Natural Product: NPC293917

Natural Product ID	NPC293917
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Bq-123
IUPAC Name	2-[(3S,6R,9S,12R,15S)-6-(1H-indol-3-ylmethyl)-9-(2-methylpropyl)-2,5,8,11,14-pentaoxo-12-propan-2-yl-1,4,7,10,13-pentazabicyclo[13.3.0]octadecan-3-yl]acetic acid
Synonyms	BQ-123
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1269102
PubChem CID	52943236
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

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 86 89 0 0 0 0 0 0 0 0999 V2000 0.0965 3.7739 -1.9377 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1307 4.1454 -0.4774 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5786 3.1815 0.4424 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1063 1.7590 0.2748 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2325 1.4746 0.4973 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 1.8576 1.1687 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1653 2.9073 2.0743 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5471 1.1794 1.0582 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5786 0.1265 0.2301 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5685 -0.8928 -0.3642 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8409 -0.8969 -1.7551 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2919 -2.2418 0.1920 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4367 -2.3699 1.6560 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0818 -2.5647 2.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1483 -2.2970 1.0372 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8981 -2.5495 -0.1204 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5708 -3.0272 -1.4008 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5849 -3.1673 -2.1131 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2273 -3.3487 -1.9089 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7665 -2.7627 -1.0192 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1183 -1.5197 -1.1086 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1242 -0.9855 -0.1904 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6989 -0.0713 0.7301 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0464 0.8878 1.0558 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1474 1.3133 2.4194 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2997 -0.5080 -1.0597 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3774 0.0527 -0.2191 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6355 1.3921 -0.0724 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6760 1.4981 0.7594 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1025 0.2888 1.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2881 -0.6393 0.5445 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5006 -1.9944 0.7768 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5308 -2.3859 1.6228 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3564 -1.4674 2.2449 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1259 -0.1333 1.9991 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4729 -0.7935 -2.1123 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0469 -4.7836 -2.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8230 -5.3565 -3.1889 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 -4.7669 -3.8637 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6732 -6.7401 -3.4413 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5987 2.2651 0.8485 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9738 1.7002 0.7302 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2899 3.1273 -0.3338 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3124 5.5577 -0.2925 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5210 2.8844 -2.1388 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1670 3.4639 -2.0413 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1443 4.6430 -2.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2113 4.0971 -0.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6488 3.1587 0.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7154 3.5185 1.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3425 1.5205 -0.8088 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5283 3.6825 2.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7266 0.8548 2.1334 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7228 -0.0655 -2.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9228 -3.0216 -0.2932 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9381 -1.5006 2.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0776 -3.2512 1.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9495 -3.6194 2.5610 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8338 -1.8839 3.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8338 -1.2204 1.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2600 -2.9129 1.2042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1089 -2.7968 -2.8694 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5728 -1.8871 0.3462 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7944 0.8515 3.0411 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9647 0.1834 -1.8498 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6968 -1.4192 -1.5517 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0705 2.1865 -0.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0763 2.4243 1.0392 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8604 -2.6910 0.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7131 -3.4282 1.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1613 -1.7572 2.9052 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7404 0.6370 2.4580 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5317 -0.9022 -2.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1317 -5.3994 -1.2539 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0977 -4.8176 -2.6035 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3144 -7.2417 -4.0306 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5618 2.8943 1.7584 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4646 1.7361 1.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8799 0.5985 0.4983 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5979 2.2062 -0.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2775 2.9613 -0.7300 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0719 3.0232 -1.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3552 4.1896 -0.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1019 6.0101 0.6512 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0940 6.1706 -1.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4117 5.6953 -0.3090 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 3 6 7 1 0 6 8 1 0 8 9 1 0 9 10 2 3 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 2 3 21 22 1 0 22 23 1 0 23 24 2 3 24 25 1 0 22 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 21 36 1 0 19 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 8 41 1 0 41 42 1 0 41 43 1 0 2 44 1 0 24 4 1 0 31 27 1 0 16 12 1 0 35 30 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 6 7 52 1 0 8 53 1 1 11 54 1 0 12 55 1 6 13 56 1 0 13 57 1 0 14 58 1 0 14 59 1 0 15 60 1 0 15 61 1 0 19 62 1 6 22 63 1 1 25 64 1 0 26 65 1 0 26 66 1 0 28 67 1 0 29 68 1 0 32 69 1 0 33 70 1 0 34 71 1 0 35 72 1 0 36 73 1 0 37 74 1 0 37 75 1 0 40 76 1 0 41 77 1 0 42 78 1 0 42 79 1 0 42 80 1 0 43 81 1 0 43 82 1 0 43 83 1 0 44 84 1 0 44 85 1 0 44 86 1 0 M END

Standard InCHIKey	VYCMAAOURFJIHD-AOYLRGCGSA-N
Standard InCHI	InChI=1S/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)/t21-,22+,23-,24-,26+/m0/s1
SMILES	CC(C[C@@H]1N=C(O)[C@H](N=C(O)[C@@H]2CCCN2C(=O)[C@@H](N=C([C@H](N=C1O)Cc1c[nH]c2c1cccc2)O)CC(=O)O)C(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.31	Volume:	611.654 ? Van der Waals volume.
Dense:	0.998	LogP:	1.115 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.402 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.245 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	31.0
TPSA:	203.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.269	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.437	Fsp³:	0.548
MCE-18:	96.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.445	Fluc inhibitor:	0.026 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.061 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.798 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.209

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.651	MDCK Permeability:	-5.102
Pgp-inhibitor:	0.889	Pgp-substrate:	0.979
PAMPA:	0.663 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.836
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.866
Plasma Protein Binding (PPB):	55.347%	Volume Distribution (VD):	-0.295
Fu:	46.455% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.077
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.162	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.984	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.981	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.019 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.371

Half-life (T1/2):

1.887

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.014	Rat Oral Acute Toxicity:	0.883
Maximum Recommended Daily Dose:	0.88	Skin Sensitization:	1.0
Carcinogencity:	0.652	Eye Corrosion:	0.0
Eye Irritation:	0.015	Respiratory Toxicity:	0.863
Drug-induced Neurotoxicity:	0.076	Ototoxicity:	0.992
Hematotoxicity:	0.612	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.217 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.193 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.767 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.881 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18071251]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	faeces	n.a.	PMID[18323202]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22874	Bombyx mori	Species	Bombycidae	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	Organism Name	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	10
Ki	5
Inhibition	2

Activity Type	# Activity
Individual protein	16
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT247	Individual protein	Endothelin receptor ET-A	Homo sapiens	IC50	=	22	nM	PMID[15055997]
NPT247	Individual protein	Endothelin receptor ET-A	Homo sapiens	Ki	=	18	nM	DOI[10.1016/0960-894X(95)00019-P]
NPT247	Individual protein	Endothelin receptor ET-A	Homo sapiens	Inhibition	=	25	%	PMID[15139753]
NPT247	Individual protein	Endothelin receptor ET-A	Homo sapiens	IC50	=	24.8	nM	PMID[20932745]
NPT304	Individual protein	Canalicular multispecific organic anion transporter 1	Rattus norvegicus	Ki	=	84100	nM	PMID[9918561]
NPT247	Individual protein	Endothelin receptor ET-A	Homo sapiens	IC50	=	20.5	nM	PMID[22862294]
NPT5167	Individual protein	Endothelin receptor ET-A	Sus scrofa	IC50	=	22	nM	DOI[10.1016/0960-894X(95)00237-N]
NPT5792	Individual protein	Endothelin receptor ET-B	Sus scrofa	IC50	=	18000	nM	DOI[10.1016/0960-894X(95)00237-N]
NPT5167	Individual protein	Endothelin receptor ET-A	Sus scrofa	IC50	=	22000	nM	PMID[1315867]
NPT5792	Individual protein	Endothelin receptor ET-B	Sus scrofa	IC50	=	23000	nM	PMID[1315867]
NPT3952	Individual protein	Endothelin receptor ET-B	Homo sapiens	IC50	>	1000	nM	PMID[22862294]
NPT3951	Individual protein	Endothelin receptor ET-A	Rattus norvegicus	IC50	=	14	nM	PMID[9667964]
NPT5168	Individual protein	Endothelin receptor ET-B	Rattus norvegicus	IC50	>	30000	nM	PMID[9667964]
NPT5168	Individual protein	Endothelin receptor ET-B	Rattus norvegicus	Ki	=	7000	nM	DOI[10.1016/0960-894X(95)00019-P]
NPT3951	Individual protein	Endothelin receptor ET-A	Rattus norvegicus	Ki	=	40	nM	PMID[9857090]
NPT5168	Individual protein	Endothelin receptor ET-B	Rattus norvegicus	Ki	=	32000	nM	PMID[9857090]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Inhibition	~	60	%	PMID[14980650]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC293917 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	27645
0.1-0.2	20376
0.2-0.3	1339
0.3-0.4	377
0.4-0.5	82
0.5-0.6	19
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	Natural Product ID
0.6837	Remote Similarity	NPC31385
0.6596	Remote Similarity	NPC489625
0.6569	Remote Similarity	NPC479075
0.6545	Remote Similarity	NPC483985
0.6429	Remote Similarity	NPC107077
0.6421	Remote Similarity	NPC213629
0.6381	Remote Similarity	NPC479073
0.6373	Remote Similarity	NPC110602
0.6373	Remote Similarity	NPC479071
0.6321	Remote Similarity	NPC479076
0.625	Remote Similarity	NPC49954
0.6238	Remote Similarity	NPC223791
0.6228	Remote Similarity	NPC489555
0.616	Remote Similarity	NPC485785
0.6132	Remote Similarity	NPC479065
0.6095	Remote Similarity	NPC155143
0.6	Remote Similarity	NPC17059
0.5963	Remote Similarity	NPC479066
0.5941	Remote Similarity	NPC483341
0.5909	Remote Similarity	NPC75726
0.5794	Remote Similarity	NPC162860
0.5726	Remote Similarity	NPC325976
0.5726	Remote Similarity	NPC326363
0.5607	Remote Similarity	NPC54420
0.5546	Remote Similarity	NPC479574
0.5489	Remote Similarity	NPC485786
0.5478	Remote Similarity	NPC100321
0.5474	Remote Similarity	NPC314603
0.5464	Remote Similarity	NPC487314
0.5315	Remote Similarity	NPC482001
0.525	Remote Similarity	NPC69843
0.5238	Remote Similarity	NPC171317
0.5194	Remote Similarity	NPC486283
0.5188	Remote Similarity	NPC485787
0.5149	Remote Similarity	NPC75634
0.5051	Remote Similarity	NPC34779

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC293917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3439
0.1-0.2	5326
0.2-0.3	326
0.3-0.4	41
0.4-0.5	14
0.5-0.6	2
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7621	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7711	Discontinued
0.5143	Remote Similarity	NPD7470	Discontinued
0.5041	Remote Similarity	NPD8493	Clinical (unspecified phase)

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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