NPASS Compound

Natural Product: NPC314603

Natural Product ID	NPC314603
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CHWWXLHSWFFSCF-LEGRXYIASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3327051
PubChem CID	NA
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 99101 0 0 0 0 0 0 0 0999 V2000 -2.7025 3.9906 -2.3391 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8462 3.2597 -1.4744 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3744 2.4408 -0.7269 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9761 1.5260 0.2548 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0704 1.2649 1.2445 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3183 0.7182 0.7218 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7323 -0.5968 0.8106 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9264 -0.7757 0.2240 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.2932 0.4341 -0.2494 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3195 1.3734 0.0449 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5208 2.6794 -0.3509 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6709 3.0184 -1.0245 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6211 2.0626 -1.3049 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4577 0.7496 -0.9256 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4069 0.2385 -0.2461 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5409 -0.7962 0.4544 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1127 -2.1508 0.2640 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0556 -2.8916 -0.5977 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7715 -4.3213 -0.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4806 -4.5603 -1.6140 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8756 -4.8421 -1.8275 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3140 -2.2385 -0.0331 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1667 -2.6829 0.8436 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5907 -2.7566 0.5226 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1663 -1.3788 0.4645 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4352 -0.8653 -0.6661 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9743 0.3922 -1.0038 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3950 1.5767 -0.3575 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4958 1.5966 0.5534 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9492 2.7465 1.1714 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0453 3.5213 0.3134 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4646 2.9540 -0.6815 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4287 3.5809 -1.5885 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8295 4.8619 0.5992 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9289 3.5853 1.9619 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3030 4.7582 2.5736 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6406 5.9742 2.3520 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2515 4.5391 3.4729 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8513 2.8541 -0.7551 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0649 0.5091 -2.5149 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7500 0.3906 -3.2102 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8582 1.7302 -2.8708 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4123 -0.6442 1.6075 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2549 -3.6549 1.5064 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1613 -3.2475 2.9364 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9097 -4.3208 3.7424 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7112 -3.3261 3.3878 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8378 -1.8574 -1.2419 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7319 0.1797 -1.4725 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7061 3.9349 -2.2263 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1294 1.9511 0.8859 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2780 2.2693 1.7291 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6567 0.6617 2.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1831 -1.3855 1.2971 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4547 -1.6758 0.1546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8071 3.4532 -0.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8395 4.0332 -1.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5275 2.3084 -1.8323 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2013 -0.0134 -1.1408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2563 -2.6182 1.3159 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2122 -2.3677 -1.5928 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1068 -2.8342 -0.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8636 -4.9744 0.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4817 -5.5854 -2.1065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4210 -4.5494 -1.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4561 -3.8608 -2.5011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0711 -4.0258 -2.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7933 -5.0671 -1.2511 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4884 -5.7055 -2.3983 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6789 -3.2277 -0.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0674 0.3630 -0.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2473 2.3468 2.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3175 4.7020 -1.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0573 3.4593 -2.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1120 5.2243 0.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7466 3.8810 1.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3521 2.9119 2.7407 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1762 6.7738 2.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5853 5.2577 3.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1732 3.6030 -0.9601 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6827 -0.3760 -2.8495 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9492 0.6001 -4.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3869 -0.6430 -3.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0079 1.1390 -2.9054 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5758 1.9194 -2.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5129 1.5179 -3.7543 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2104 2.6119 -3.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3342 -0.1808 1.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3528 -3.7956 1.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8101 -4.6705 1.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6364 -2.3064 3.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5119 -5.3171 3.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9750 -4.3016 3.4447 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7632 -4.1732 4.8181 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2295 -2.3129 3.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6222 -3.6306 4.4544 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1457 -4.0739 2.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4415 -2.4246 -1.8074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1248 -0.4246 -2.2146 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 4 15 1 0 15 16 2 3 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 17 22 1 0 22 23 2 3 23 24 1 0 24 25 1 0 25 26 2 3 26 27 1 0 27 28 1 0 28 29 2 3 29 30 1 0 30 31 1 0 31 32 2 3 32 33 1 0 31 34 1 0 30 35 1 0 35 36 1 0 36 37 2 3 36 38 1 0 28 39 1 0 27 40 1 0 40 41 1 0 40 42 1 0 25 43 1 0 24 44 1 0 44 45 1 0 45 46 1 0 45 47 1 0 22 48 1 0 15 49 1 0 33 2 1 0 10 6 1 0 14 9 1 0 1 50 1 0 4 51 1 1 5 52 1 0 5 53 1 0 7 54 1 0 8 55 1 0 11 56 1 0 12 57 1 0 13 58 1 0 14 59 1 0 17 60 1 1 18 61 1 0 18 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 20 66 1 0 21 67 1 0 21 68 1 0 21 69 1 0 24 70 1 6 27 71 1 1 30 72 1 1 33 73 1 0 33 74 1 0 34 75 1 0 35 76 1 0 35 77 1 0 37 78 1 0 38 79 1 0 39 80 1 0 40 81 1 0 41 82 1 0 41 83 1 0 41 84 1 0 42 85 1 0 42 86 1 0 42 87 1 0 43 88 1 0 44 89 1 0 44 90 1 0 45 91 1 0 46 92 1 0 46 93 1 0 46 94 1 0 47 95 1 0 47 96 1 0 47 97 1 0 48 98 1 0 49 99 1 0 M END

Standard InCHIKey	CHWWXLHSWFFSCF-LEGRXYIASA-N
Standard InCHI	InChI=1S/C34H50N8O7/c1-17(2)11-23-31(46)40-24(12-18(3)4)33(48)42-29(19(5)6)34(49)41-26(14-27(35)43)30(45)37-16-28(44)38-25(32(47)39-23)13-20-15-36-22-10-8-7-9-21(20)22/h7-10,15,17-19,23-26,29,36H,11-14,16H2,1-6H3,(H2,35,43)(H,37,45)(H,38,44)(H,39,47)(H,40,46)(H,41,49)(H,42,48)/t23-,24+,25-,26-,29-/m0/s1
SMILES	OC1=N[C@@H](Cc2c[nH]c3c2cccc3)C(=N[C@@H](CC(C)C)C(=N[C@@H](C(=N[C@H](C(=N[C@H](C(=NC1)O)CC(=N)O)O)C(C)C)O)CC(C)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	682.38	Volume:	691.455 ? Van der Waals volume.
Dense:	0.987	LogP:	1.641 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.479 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.855 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	29.0
TPSA:	255.41 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	3.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.113	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.015	Fsp³:	0.559
MCE-18:	87.113 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.721	Fluc inhibitor:	0.249 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.134 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.934 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.095

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.045	MDCK Permeability:	-5.168
Pgp-inhibitor:	0.226	Pgp-substrate:	0.995
PAMPA:	0.987 ? 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):	0.858
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:	0.779
Plasma Protein Binding (PPB):	46.514%	Volume Distribution (VD):	-0.183
Fu:	53.763% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.012
BSEP inhibitor:	0.839

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.046	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.289 ? 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):

0.244

Half-life (T1/2):

1.988

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:	0.054	Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.794	Skin Sensitization:	1.0
Carcinogencity:	0.977	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.901
Drug-induced Neurotoxicity:	0.087	Ototoxicity:	0.999
Hematotoxicity:	0.424	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.219 ? 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:	3.239 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.787 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.851 ? 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
NPO13227.1	Streptomyces scopuliridis SCSIO ZJ46	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25072108]
NPO13227.1	Streptomyces scopuliridis SCSIO ZJ46	Strain	Streptomycetaceae	Bacteria	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
MIC	5
IC50	4

Activity Type	# Activity
Cell line	4
Organism	5

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[25072108]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	>	100000.0	nM	PMID[25072108]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[25072108]
NPT395	Cell line	SF-268	Homo sapiens	IC50	>	100000.0	nM	PMID[25072108]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	12.5	ug.mL-1	PMID[25072108]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	128.0	ug.mL-1	PMID[25072108]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[25072108]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[25072108]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	128.0	ug.mL-1	PMID[25072108]

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 NPC314603 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	28324
0.1-0.2	19806
0.2-0.3	1288
0.3-0.4	339
0.4-0.5	68
0.5-0.6	26
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9155	High Similarity	NPC34779
0.7206	Intermediate Similarity	NPC49954
0.6892	Remote Similarity	NPC160105
0.6818	Remote Similarity	NPC483341
0.6765	Remote Similarity	NPC279918
0.6596	Remote Similarity	NPC155143
0.5943	Remote Similarity	NPC483985
0.5778	Remote Similarity	NPC482066
0.5747	Remote Similarity	NPC487314
0.5735	Remote Similarity	NPC59269
0.5714	Remote Similarity	NPC213629
0.5556	Remote Similarity	NPC282231
0.5474	Remote Similarity	NPC293917
0.5455	Remote Similarity	NPC69843
0.5405	Remote Similarity	NPC63751
0.5354	Remote Similarity	NPC31385
0.5333	Remote Similarity	NPC54988
0.5294	Remote Similarity	NPC479075
0.5268	Remote Similarity	NPC325976
0.5268	Remote Similarity	NPC326363
0.5196	Remote Similarity	NPC479572
0.5196	Remote Similarity	NPC479568
0.5196	Remote Similarity	NPC479573
0.5196	Remote Similarity	NPC479566
0.5196	Remote Similarity	NPC479567
0.5196	Remote Similarity	NPC479569
0.5196	Remote Similarity	NPC479571
0.5146	Remote Similarity	NPC479570
0.5143	Remote Similarity	NPC479073
0.5102	Remote Similarity	NPC107077
0.5094	Remote Similarity	NPC479076
0.5063	Remote Similarity	NPC192615

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC314603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3270
0.1-0.2	5591
0.2-0.3	223
0.3-0.4	51
0.4-0.5	11
0.5-0.6	4
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
0.5474	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5426	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.5301	Remote Similarity	NPD4184	Phase 2
0.5192	Remote Similarity	NPD8272	Phase 2

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