NPASS Compound

Natural Product: NPC481315

Natural Product ID	NPC481315
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ILRUNDIYZZKEFA-JCTZSOHTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	132577489
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 87 91 0 0 0 0 0 0 0 0999 V2000 -5.3480 2.0641 -0.1740 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0763 0.8446 0.6819 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6395 1.0105 2.0615 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7110 -0.3440 -0.0169 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9751 -1.6313 0.2684 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5725 -1.6095 -0.3640 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7109 -2.4382 0.5358 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2976 -2.4064 0.0885 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7135 -1.0522 0.1231 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5904 -0.6289 1.5907 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6280 -0.0288 -0.5013 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1763 1.0005 -1.1616 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2777 1.3167 -1.3976 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0636 0.4939 -0.4235 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5151 0.8061 -0.3653 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1435 1.0995 -1.7178 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6801 2.0645 0.4642 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1379 1.8221 1.8638 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3633 1.0120 2.0147 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6034 0.0436 0.8199 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5649 0.7056 -0.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3094 -1.1754 1.3771 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6162 -2.0765 0.3800 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2527 -0.3005 0.3586 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0310 -1.5483 -0.4061 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5683 -1.9607 -0.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6226 -0.9135 -0.6076 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3139 -1.2944 -2.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5148 1.7472 2.2465 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0803 1.3711 2.6896 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4469 2.6802 -1.3229 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6535 3.3321 -2.5141 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1193 -0.1965 -0.3744 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5795 0.5967 0.8152 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6352 -2.1455 -1.7406 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3336 -1.4279 -2.7249 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0298 -3.4572 -1.9794 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2232 1.8796 -0.8553 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5581 2.9683 0.4046 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4936 2.2648 -0.8547 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6460 1.4888 2.0354 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7187 0.0531 2.5864 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9997 1.6935 2.6591 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6803 -0.1924 -1.1199 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7466 -0.4833 0.3487 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9324 -1.8594 1.3414 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5321 -2.4392 -0.2358 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9056 -2.0931 1.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0791 -3.5123 0.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2383 -2.9370 -0.8785 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7079 -3.0496 0.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9736 0.4265 1.7397 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2437 -1.2402 2.2470 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4205 -0.7448 1.9931 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8722 1.7136 -1.5935 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4105 1.0381 -2.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6627 0.8226 0.5918 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4211 0.9441 -2.5680 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9666 0.3855 -1.9645 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4358 2.1656 -1.8310 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 2.5884 0.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3181 2.8298 0.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3695 2.8500 2.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2259 0.3413 2.8881 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3224 1.6806 -0.4813 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0124 -0.0143 -0.8300 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4767 0.9126 0.5761 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7395 -1.6342 2.2123 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2896 -0.8053 1.7855 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4752 -2.5291 0.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6534 -0.4304 1.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6175 -2.4253 -0.1756 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0612 -1.4178 -1.5096 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3699 -2.9194 -0.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5069 -2.0754 0.9701 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2997 -2.4279 -2.1009 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6747 -1.0000 -2.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1324 -1.0390 -2.7489 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1749 1.2368 2.8112 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4555 0.7641 3.3945 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2396 3.1347 -3.1474 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5966 3.1323 -3.0061 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5653 4.4384 -2.2807 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6043 0.2935 -1.2712 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3398 0.1181 1.7879 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0879 1.5890 0.7757 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7833 -3.8593 -2.8749 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 19 29 1 0 18 30 1 0 13 31 1 0 31 32 1 0 11 33 1 0 33 34 1 0 6 35 1 6 35 36 2 0 35 37 1 0 34 2 1 0 33 6 1 0 27 9 1 0 27 14 1 0 24 15 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 5 46 1 0 5 47 1 0 7 48 1 0 7 49 1 0 8 50 1 0 8 51 1 0 10 52 1 0 10 53 1 0 10 54 1 0 12 55 1 0 13 56 1 6 14 57 1 1 16 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 1 19 64 1 1 21 65 1 0 21 66 1 0 21 67 1 0 22 68 1 0 22 69 1 0 23 70 1 0 24 71 1 1 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 28 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 30 80 1 0 32 81 1 0 32 82 1 0 32 83 1 0 33 84 1 6 34 85 1 0 34 86 1 0 37 87 1 0 M END

Standard InCHIKey	ILRUNDIYZZKEFA-JCTZSOHTSA-N
Standard InCHI	InChI=1S/C31H50O6/c1-26(2)10-12-31(25(35)36)13-11-29(5)18(19(31)15-26)14-21(37-7)23-27(3)16-20(33)24(34)28(4,17-32)22(27)8-9-30(23,29)6/h14,19-24,32-34H,8-13,15-17H2,1-7H3,(H,35,36)/t19-,20+,21+,22+,23+,24-,27-,28-,29+,30+,31-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=C[C@H]([C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O)O)OC)[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.36	Volume:	549.418 ? Van der Waals volume.
Dense:	0.943	LogP:	2.385 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.549 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.595 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	107.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.4	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.21	Fsp³:	0.903
MCE-18:	109.797 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.642	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.252	Promiscuous compounds:	0.255

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.54	MDCK Permeability:	-5.15
Pgp-inhibitor:	0.0	Pgp-substrate:	0.007
PAMPA:	1.0 ? 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):	0.017
20% Bioavailability (F20%):	0.82	30% Bioavailability (F30%):	0.057
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.654	MRP1:	0.907
Plasma Protein Binding (PPB):	85.001%	Volume Distribution (VD):	-0.244
Fu:	13.033% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.66	BCRP inhibitor:	0.008
BSEP inhibitor:	0.678

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.01
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.437
HLM stability:	0.663 ? 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):

3.234

Half-life (T1/2):

1.376

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.09
Human Hepatotoxicity (H-HT):	0.674	Drug-induced Liver Injury (DILI):	0.524
AMES Toxicity:	0.335	Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.101	Skin Sensitization:	0.864
Carcinogencity:	0.704	Eye Corrosion:	0.002
Eye Irritation:	0.556	Respiratory Toxicity:	0.403
Drug-induced Neurotoxicity:	0.036	Ototoxicity:	0.839
Hematotoxicity:	0.328	Drug-induced Nephrotoxicity:	0.875
Genotoxicity:	0.11	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.029	Hek293 Cytotoxicity:	0.072
BCF:	1.067 ? 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:	3.643 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.352 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.452 ? 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
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27797185]
NPO4734	Syzygium nervosum	Species	Myrtaceae	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	3
GI	1
Inhibition	6

Activity Type	# Activity
Cell line	10

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
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[27797185]
NPT465	Cell line	NCI-N87	Homo sapiens	IC50	>	10000.0	nM	PMID[27797185]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	GI	<	5.0	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	68.8	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	64.8	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	42.3	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	52.8	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	54.1	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	22.0	%	PMID[27797185]

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 NPC481315 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	16784
0.1-0.2	29699
0.2-0.3	2900
0.3-0.4	311
0.4-0.5	114
0.5-0.6	39
0.6-0.7	3
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
0.7397	Intermediate Similarity	NPC481319
0.7286	Intermediate Similarity	NPC91010
0.7246	Intermediate Similarity	NPC481314
0.7	Intermediate Similarity	NPC231063
0.7	Intermediate Similarity	NPC282395
0.6712	Remote Similarity	NPC481316
0.6081	Remote Similarity	NPC110308
0.6081	Remote Similarity	NPC609452
0.5946	Remote Similarity	NPC307282
0.5946	Remote Similarity	NPC84319
0.5946	Remote Similarity	NPC52021
0.5946	Remote Similarity	NPC599947
0.5867	Remote Similarity	NPC88116
0.5714	Remote Similarity	NPC201657
0.5584	Remote Similarity	NPC40092
0.5584	Remote Similarity	NPC145667
0.557	Remote Similarity	NPC481318
0.5526	Remote Similarity	NPC270768
0.5526	Remote Similarity	NPC59263
0.5526	Remote Similarity	NPC210106
0.5455	Remote Similarity	NPC173744
0.5455	Remote Similarity	NPC204961
0.5455	Remote Similarity	NPC73004
0.5455	Remote Similarity	NPC481360
0.5385	Remote Similarity	NPC32407
0.5385	Remote Similarity	NPC263548
0.5385	Remote Similarity	NPC606320
0.5375	Remote Similarity	NPC20235
0.5375	Remote Similarity	NPC299996
0.5316	Remote Similarity	NPC247139
0.5256	Remote Similarity	NPC106112
0.5256	Remote Similarity	NPC261935
0.5256	Remote Similarity	NPC472149
0.525	Remote Similarity	NPC607666
0.525	Remote Similarity	NPC608261
0.525	Remote Similarity	NPC611078
0.5195	Remote Similarity	NPC480946
0.5195	Remote Similarity	NPC130577
0.5195	Remote Similarity	NPC142415
0.5195	Remote Similarity	NPC102683
0.5185	Remote Similarity	NPC117663
0.5181	Remote Similarity	NPC481320
0.5128	Remote Similarity	NPC32118
0.5122	Remote Similarity	NPC479743
0.5119	Remote Similarity	NPC80566
0.51	Remote Similarity	NPC473405
0.5063	Remote Similarity	NPC158141

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC481315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5559
0.1-0.2	3536
0.2-0.3	50
0.3-0.4	5
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