NPASS Compound

Natural Product: NPC479688

Natural Product ID	NPC479688
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YCLLGOAXHSTFQF-VIRHFZLLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 84 92 0 0 0 0 0 0 0 0999 V2000 -3.6260 -3.9668 -0.9130 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4380 -3.0592 -1.8469 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2539 -2.1923 -1.8301 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6494 -0.7376 -1.7127 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4172 0.1454 -1.5047 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1911 -0.6774 -1.5056 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8536 -0.3299 -0.7219 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6114 0.1108 0.6361 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0788 -0.9663 1.5943 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1957 -2.1627 1.4189 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1042 -1.9016 1.8277 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6953 -2.6289 2.8771 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3356 -3.9381 2.6545 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3519 -3.9947 1.5410 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6888 -4.1631 0.1838 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5651 -0.5440 1.7583 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8549 0.4306 0.9202 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8004 1.7423 1.7408 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8520 2.8466 0.7363 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3788 3.6846 0.7307 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0525 4.9757 0.5180 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3290 4.7265 0.0249 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5657 5.3053 -0.2975 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 4.0196 -0.6142 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5802 2.8669 -1.0302 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4521 2.3485 -0.3905 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6127 0.8948 -0.2504 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7141 3.8816 1.1196 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1654 -0.4920 -1.3569 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3881 -0.1199 -0.8809 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5550 -0.3861 -1.6122 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5135 -1.0269 -2.8267 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2799 -1.3947 -3.2930 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2060 -1.1281 -2.5793 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6307 0.1186 -0.8760 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9779 0.1114 -1.1550 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8255 0.6897 -0.2363 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3117 1.2523 0.9215 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9350 1.2403 1.1704 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1003 0.6646 0.2539 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7470 0.5130 0.2366 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3278 0.9901 -2.5998 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5109 -4.5992 -0.9525 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1705 -2.9475 -2.6452 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7035 -2.3410 -2.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5203 -2.4774 -1.0817 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2685 -0.6497 -0.8282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1156 -0.4354 -2.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0469 -1.5755 -2.1200 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2109 1.0112 0.8295 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1001 -1.3020 1.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0462 -0.6127 2.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6234 -2.9709 2.0906 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3480 -2.5673 0.3973 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4697 -1.9391 3.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9171 -2.6771 3.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6238 -4.7932 2.5969 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9293 -4.1664 3.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1057 -4.7923 1.7036 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9299 -3.0317 1.5966 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -3.7834 0.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5033 -5.3199 0.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6379 -0.2302 2.8496 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6443 -0.5867 1.4639 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 1.8281 2.4010 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1093 1.7949 2.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4027 3.3493 0.8758 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5290 5.8572 0.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0773 4.1513 -0.9280 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6279 5.9812 -1.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0719 5.7918 0.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0743 4.2743 -1.4190 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9764 3.7441 0.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2942 3.0579 -2.1129 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3346 2.0345 -1.1510 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7117 0.8101 0.0279 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4352 -1.2110 -3.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2348 -1.9086 -4.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3336 -0.3344 -2.0624 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8944 0.6913 -0.4441 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9472 1.7110 1.6575 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4994 1.6687 2.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1123 0.8382 0.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0986 0.9087 -3.2120 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 11 16 1 0 16 17 1 0 17 18 1 1 19 18 1 1 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 22 28 1 0 7 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 31 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 5 42 1 6 15 1 1 0 27 17 1 0 34 29 1 0 40 35 1 0 27 5 1 0 41 30 1 0 17 8 1 0 26 19 1 0 28 19 1 0 1 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 4 47 1 0 4 48 1 0 6 49 1 0 8 50 1 1 9 51 1 0 9 52 1 0 10 53 1 0 10 54 1 0 12 55 1 0 12 56 1 0 13 57 1 0 13 58 1 0 14 59 1 0 14 60 1 0 15 61 1 0 15 62 1 0 16 63 1 0 16 64 1 0 18 65 1 0 18 66 1 0 20 67 1 0 21 68 1 0 22 69 1 6 23 70 1 0 23 71 1 0 24 72 1 0 24 73 1 0 25 74 1 0 25 75 1 0 27 76 1 1 32 77 1 0 33 78 1 0 36 79 1 0 37 80 1 0 38 81 1 0 39 82 1 0 41 83 1 0 42 84 1 0 M END

Standard InCHIKey	YCLLGOAXHSTFQF-VIRHFZLLSA-N
Standard InCHI	InChI=1S/C36H42N4O2/c41-35-16-7-3-1-2-4-8-19-39-21-15-29(34(24-39)23-36-17-13-25(42-36)10-9-20-40(36)33(34)35)28(22-35)31-32-27(14-18-37-31)26-11-5-6-12-30(26)38-32/h1,3,5-6,11-14,17-18,22,25,29,33,38,41H,2,4,7-10,15-16,19-21,23-24H2/b3-1-/t25-,29-,33+,34-,35-,36-/m0/s1
SMILES	C1=CCC[C@@]2(C=C([C@@H]3CCN(CCCC1)C[C@]13C[C@@]34C=C[C@H](CCCN3[C@@H]21)O4)c1c2c(ccn1)c1ccccc1[nH]2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.33	Volume:	592.043 ? Van der Waals volume.
Dense:	0.95	LogP:	3.986 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.349 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.162 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	48.0
TPSA:	64.62 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	9.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.346	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.422	Fsp³:	0.528
MCE-18:	220.473 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.47	Fluc inhibitor:	0.019 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.825 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.652 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.773

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.401	MDCK Permeability:	-5.077
Pgp-inhibitor:	0.001	Pgp-substrate:	0.032
PAMPA:	0.003 ? 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):	0.0
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.245
50% Bioavailability (F50%):	0.751

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1.0	MRP1:	0.998
Plasma Protein Binding (PPB):	88.028%	Volume Distribution (VD):	0.111
Fu:	9.933% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.024
OATP1B3 inhibitor:	0.045	BCRP inhibitor:	0.086
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.895	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.972	CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.957	CYP3A4-substrate:	0.15
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.449 ? 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):

10.242

Half-life (T1/2):

0.816

ADMET: Toxicity

hERG Blockers:	0.792	hERG Blockers (10um):	0.434
Human Hepatotoxicity (H-HT):	0.591	Drug-induced Liver Injury (DILI):	0.332
AMES Toxicity:	0.394	Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.993	Skin Sensitization:	0.997
Carcinogencity:	0.561	Eye Corrosion:	0.0
Eye Irritation:	0.051	Respiratory Toxicity:	0.991
Drug-induced Neurotoxicity:	0.917	Ototoxicity:	0.809
Hematotoxicity:	0.332	Drug-induced Nephrotoxicity:	0.982
Genotoxicity:	0.935	RPMI-8226 Immunitoxicity:	0.367
A549 Cytotoxicity:	0.988	Hek293 Cytotoxicity:	0.966
BCF:	1.933 ? 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:	4.0 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.15 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.778 ? 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
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332848]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2004-Mar	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2002-May	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28452477]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	3
MIC	6

Activity Type	# Activity
Individual protein	1
Organism	6
Protein complex	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1821	Individual protein	Sortase	Staphylococcus aureus	IC50	>	150000.0	nM	PMID[28452477]
NPT2890	Protein complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	150000.0	nM	PMID[28452477]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	0.0031	ug.mL-1	PMID[28452477]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.1	ug.mL-1	PMID[28452477]
NPT25245	Organism	Proteus hauseri	Proteus hauseri	MIC	>	0.1	ug.mL-1	PMID[28452477]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.1	ug.mL-1	PMID[28452477]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	0.1	ug.mL-1	PMID[28452477]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	0.05	ug.mL-1	PMID[28452477]
NPT2	Others	Unspecified	n.a.	IC50	=	140000.0	nM	PMID[28452477]

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 NPC479688 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	33772
0.1-0.2	15772
0.2-0.3	252
0.3-0.4	29
0.4-0.5	7
0.5-0.6	15
0.6-0.7	8
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	Natural Product ID
0.7944	Intermediate Similarity	NPC471506
0.7477	Intermediate Similarity	NPC476492
0.7034	Intermediate Similarity	NPC476493
0.6887	Remote Similarity	NPC166492
0.6822	Remote Similarity	NPC473362
0.6724	Remote Similarity	NPC81175
0.6696	Remote Similarity	NPC473310
0.6577	Remote Similarity	NPC189202
0.6577	Remote Similarity	NPC479685
0.6562	Remote Similarity	NPC471564
0.6455	Remote Similarity	NPC473757
0.5862	Remote Similarity	NPC607194
0.5826	Remote Similarity	NPC487892
0.5826	Remote Similarity	NPC6215
0.5702	Remote Similarity	NPC909
0.5702	Remote Similarity	NPC41679
0.5702	Remote Similarity	NPC475338
0.5641	Remote Similarity	NPC476451
0.5641	Remote Similarity	NPC253069
0.5641	Remote Similarity	NPC607417
0.562	Remote Similarity	NPC479681
0.5528	Remote Similarity	NPC473312
0.5528	Remote Similarity	NPC160752
0.55	Remote Similarity	NPC265576
0.5234	Remote Similarity	NPC476491
0.5159	Remote Similarity	NPC475258

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5798
0.1-0.2	3316
0.2-0.3	36
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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
		NPD

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