NPASS Compound

Natural Product: NPC19336

Natural Product ID	NPC19336
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sapinsignoid A
IUPAC Name	n.a.
Synonyms	Sapinsignoid A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2042140
PubChem CID	57408526
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

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 97100 0 0 0 0 0 0 0 0999 V2000 12.1907 0.2880 0.3591 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6686 0.4500 0.5615 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9486 -0.7195 -0.0420 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4449 -0.5631 0.1962 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8967 0.6689 -0.4279 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4347 0.8924 -0.3404 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7446 1.0448 0.9369 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7067 -0.0596 1.9110 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0591 -1.2980 1.3143 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6621 -0.9943 0.9083 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2711 -1.0649 -0.3465 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9009 -0.7689 -0.7582 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5100 -0.8392 -2.0179 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1207 -0.5361 -2.4090 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2510 -0.5999 -3.5944 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7584 -0.1803 -1.4298 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1399 0.1368 -1.6741 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9113 -0.9510 -2.2801 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2205 -1.3235 -1.6638 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4492 -2.8015 -1.8166 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2660 -0.8197 -0.2833 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2126 0.7073 -0.3826 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7607 1.0140 -0.6791 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3812 1.5647 -2.0109 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5130 1.9171 -2.9793 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2811 2.5797 -2.0395 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6913 2.7501 -0.7885 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2813 3.3351 0.3185 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4667 3.7696 0.1838 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5708 3.4607 1.6267 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6854 1.2537 0.8951 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9240 1.2139 1.3508 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1754 1.8346 2.6793 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1125 2.8702 2.5497 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1329 0.6140 0.6916 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7431 -0.7519 0.1933 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3847 -1.2044 0.5909 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5013 -2.6220 0.8908 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7609 -2.9282 1.1060 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5879 -1.7367 0.9662 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7434 -1.5608 1.3901 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3257 -4.2877 1.4494 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0626 -0.9428 -1.1359 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0724 -1.2212 0.3624 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0133 -2.3015 2.2974 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5540 -0.5626 0.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6918 1.2160 0.7123 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3849 0.1746 -0.7159 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4375 0.5176 1.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3515 1.4031 0.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2396 -1.6414 0.5052 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1450 -0.8025 -1.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3890 -0.4915 1.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9168 -1.4860 -0.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1759 0.6601 -1.5242 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4407 1.5723 -0.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8918 0.0788 -0.9486 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1636 1.8201 -0.9682 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1573 1.9712 1.4610 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6708 1.3259 0.7022 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 -0.2642 2.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9016 0.2707 2.6909 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6241 -1.6641 0.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9707 -0.7109 1.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9852 -1.3527 -1.0953 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2032 -0.4848 0.0171 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2594 -1.1299 -2.7469 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2976 -1.9040 -2.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0693 -0.7293 -3.3772 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0298 -0.8360 -2.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3632 -3.0187 -2.9228 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6481 -3.4194 -1.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4592 -3.1368 -1.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8895 0.9905 -1.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1959 1.1593 0.2581 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1130 2.4889 -3.8416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2200 2.6318 -2.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0350 1.0411 -3.3782 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4521 2.2815 -2.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7094 3.5659 -2.3535 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2623 2.7384 1.7046 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2620 3.2706 2.4760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2375 4.5106 1.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9737 1.7352 1.5350 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6376 1.0763 3.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2563 2.2577 3.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2716 3.3290 3.3963 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9932 0.6309 1.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2950 1.2407 -0.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1799 -0.7015 1.5888 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6943 -3.3332 0.9355 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5581 -5.0717 1.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6555 -4.3063 2.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2306 -4.4741 0.8357 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5259 -0.1409 -1.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2407 -1.6891 1.2009 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8838 -1.8964 3.1886 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 17 16 1 1 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 22 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 36 43 1 6 21 44 1 1 9 45 1 0 23 17 1 0 40 36 1 0 24 17 1 0 37 21 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 8 61 1 0 8 62 1 0 9 63 1 6 10 64 1 0 11 65 1 0 12 66 1 0 13 67 1 0 18 68 1 0 18 69 1 0 19 70 1 6 20 71 1 0 20 72 1 0 20 73 1 0 22 74 1 6 23 75 1 1 25 76 1 0 25 77 1 0 25 78 1 0 26 79 1 0 26 80 1 0 30 81 1 0 30 82 1 0 30 83 1 0 31 84 1 0 33 85 1 0 33 86 1 0 34 87 1 0 35 88 1 0 35 89 1 0 37 90 1 1 38 91 1 0 42 92 1 0 42 93 1 0 42 94 1 0 43 95 1 0 44 96 1 0 45 97 1 0 M END

Standard InCHIKey	YTMXKWFNNGHMHW-RMRDEULQSA-N
Standard InCHI	InChI=1S/C36H52O9/c1-6-7-8-9-10-11-14-27(39)15-12-13-16-30(40)45-35-19-24(3)36(43)28(31(35)33(35,5)22-44-25(4)38)18-26(21-37)20-34(42)29(36)17-23(2)32(34)41/h12-13,15-18,24,27-29,31,37,39,42-43H,6-11,14,19-22H2,1-5H3/b15-12+,16-13+/t24-,27-,28+,29-,31-,33-,34-,35+,36-/m1/s1
SMILES	CCCCCCCC[C@H](/C=C/C=C/C(=O)O[C@@]12C[C@@H](C)[C@]3([C@H]([C@@H]1[C@@]2(C)COC(=O)C)C=C(CO)C[C@]1([C@H]3C=C(C1=O)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	628.36	Volume:	657.643 ? Van der Waals volume.
Dense:	0.955	LogP:	3.422 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.272 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.793 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	23.0
TPSA:	150.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.073	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.444	Fsp³:	0.694
MCE-18:	79.148 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.579	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.023 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.2	Promiscuous compounds:	0.598

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.081	MDCK Permeability:	-4.693
Pgp-inhibitor:	0.002	Pgp-substrate:	0.983
PAMPA:	0.989 ? 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):	0.295
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.556
Plasma Protein Binding (PPB):	90.294%	Volume Distribution (VD):	0.126
Fu:	8.453% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.017
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.964
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.841 ? 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):

3.119

Half-life (T1/2):

1.186

ADMET: Toxicity

hERG Blockers:	0.139	hERG Blockers (10um):	0.407
Human Hepatotoxicity (H-HT):	0.682	Drug-induced Liver Injury (DILI):	0.289
AMES Toxicity:	0.441	Rat Oral Acute Toxicity:	0.279
Maximum Recommended Daily Dose:	0.591	Skin Sensitization:	0.989
Carcinogencity:	0.536	Eye Corrosion:	0.029
Eye Irritation:	0.586	Respiratory Toxicity:	0.849
Drug-induced Neurotoxicity:	0.105	Ototoxicity:	0.611
Hematotoxicity:	0.624	Drug-induced Nephrotoxicity:	0.603
Genotoxicity:	0.029	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.445	Hek293 Cytotoxicity:	0.202
BCF:	0.837 ? 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:	4.062 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.041 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.053 ? 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
NPO158	Sapium insigne	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22409148]
NPO158	Sapium insigne	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO158	Sapium insigne	Species	Euphorbiaceae	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	2

Activity Type	# Activity
Cell line	2

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
NPT81	Cell line	A549	Homo sapiens	IC50	=	1800.0	nM	PMID[12828466]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	3400.0	nM	Open TG-GATES in vivo data: Biochemistry

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 NPC19336 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	16815
0.1-0.2	31003
0.2-0.3	1904
0.3-0.4	60
0.4-0.5	50
0.5-0.6	20
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
1.0	High Similarity	NPC185876
0.7901	Intermediate Similarity	NPC180640
0.7195	Intermediate Similarity	NPC153651
0.6395	Remote Similarity	NPC472760
0.6145	Remote Similarity	NPC474872
0.587	Remote Similarity	NPC479001
0.587	Remote Similarity	NPC479002
0.5854	Remote Similarity	NPC485736
0.5854	Remote Similarity	NPC277477
0.5854	Remote Similarity	NPC479003
0.5854	Remote Similarity	NPC485735
0.5769	Remote Similarity	NPC153036
0.5714	Remote Similarity	NPC482454
0.5698	Remote Similarity	NPC485732
0.5432	Remote Similarity	NPC158523
0.5341	Remote Similarity	NPC477091
0.5301	Remote Similarity	NPC71889
0.5301	Remote Similarity	NPC475937
0.5169	Remote Similarity	NPC475391
0.5165	Remote Similarity	NPC484333
0.5114	Remote Similarity	NPC170212
0.5109	Remote Similarity	NPC145238
0.5055	Remote Similarity	NPC474937
0.5053	Remote Similarity	NPC482199
0.5053	Remote Similarity	NPC482197

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC19336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6554
0.1-0.2	2563
0.2-0.3	33
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