NPASS Compound

Natural Product: NPC488545

Natural Product ID	NPC488545
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SNSZEFPBNADANW-ZVLRDVKFSA-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] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

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 82 89 0 0 0 0 0 0 0 0999 V2000 -7.4168 1.3406 -1.8335 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0319 2.5530 -1.9767 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1984 2.8170 -1.3146 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7282 1.8298 -0.5062 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0910 0.6035 -0.3716 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9161 0.3210 -1.0307 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1993 -0.9846 -0.9159 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7334 -1.8577 0.1661 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8880 -2.7488 -0.3016 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3238 -3.4827 0.7859 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7463 -2.7844 0.6372 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4291 -2.4150 0.7846 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5557 -3.0778 1.6263 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2496 -2.6523 1.7243 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7662 -1.5751 1.0070 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6366 -0.9202 0.1731 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9637 -1.3387 0.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8353 -0.6784 -0.7764 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3464 -1.1801 1.1678 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9934 0.1273 0.5524 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2790 0.0192 -0.7664 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0254 -0.3285 -0.5169 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3154 -0.1139 0.8025 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6066 0.5762 1.0011 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7900 1.6237 1.8656 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0453 2.2156 1.9890 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1211 1.7724 1.2577 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9484 0.7210 0.3865 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6885 0.1367 0.2709 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0340 0.2836 -0.3428 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2255 1.0330 -0.4703 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3149 0.1717 -0.9342 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1612 0.6112 -1.9299 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1967 -0.1758 -2.3887 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3996 -1.4228 -1.8525 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5674 -1.8790 -0.8598 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5269 -1.0787 -0.4041 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7807 -3.1449 -0.3214 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4443 -2.2477 -2.2981 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5450 1.6824 0.8677 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5748 2.7811 0.5884 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0988 3.6767 -0.3532 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3843 2.3337 1.3520 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1670 0.5638 1.4624 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2656 -0.0102 2.7638 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9467 -1.1637 2.4891 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9029 2.0806 0.1674 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8311 4.0292 -1.4458 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5041 1.1568 -2.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5756 3.3033 -2.6266 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5555 -0.1055 0.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2842 -1.5594 -1.8788 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0589 -1.2253 1.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6584 -2.2123 -0.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4759 -3.5107 -1.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5142 -3.9489 1.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9519 -3.9284 2.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5957 -3.1955 2.3927 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3047 -0.0708 -0.4105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7479 -1.9806 0.6423 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7895 0.8787 0.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2593 1.0486 -1.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7952 -0.6375 -1.4974 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4320 -1.1293 1.2846 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9373 1.9576 2.4297 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1871 3.0430 2.6731 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5791 -0.6931 -0.4248 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0546 1.8997 -1.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0471 1.5948 -2.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8263 0.2152 -3.1653 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9055 -1.4975 0.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3003 -3.8366 -0.8761 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2694 -2.3031 -1.7094 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9542 0.9334 1.5480 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5253 2.3367 0.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8349 3.3401 1.5109 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1129 3.7575 -0.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1848 1.6655 1.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8502 0.7451 3.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6329 -0.2660 3.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7431 1.5552 -0.0279 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8062 4.0263 -1.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 8 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 15 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 35 39 1 0 31 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 23 44 1 0 44 45 1 0 45 46 1 0 4 47 1 0 3 48 1 0 6 1 1 0 18 7 1 0 46 19 1 0 17 12 1 0 44 20 1 0 29 24 1 0 37 32 1 0 43 27 1 0 1 49 1 0 2 50 1 0 5 51 1 0 7 52 1 6 8 53 1 1 9 54 1 0 9 55 1 0 10 56 1 0 13 57 1 0 14 58 1 0 16 59 1 0 19 60 1 6 20 61 1 6 21 62 1 0 21 63 1 0 23 64 1 1 25 65 1 0 26 66 1 0 29 67 1 0 31 68 1 6 33 69 1 0 34 70 1 0 37 71 1 0 38 72 1 0 39 73 1 0 40 74 1 1 41 75 1 0 41 76 1 0 42 77 1 0 44 78 1 1 45 79 1 0 45 80 1 0 47 81 1 0 48 82 1 0 M END

Standard InCHIKey	SNSZEFPBNADANW-ZVLRDVKFSA-N
Standard InCHI	InChI=1S/C36H34O12/c37-13-31-35(17-1-5-23(39)25(41)9-17)47-29-11-19(3-7-27(29)45-31)33-21-15-44-34(22(21)16-43-33)20-4-8-28-30(12-20)48-36(32(14-38)46-28)18-2-6-24(40)26(42)10-18/h1-12,21-22,31-42H,13-16H2/t21-,22-,31-,32-,33+,34+,35-,36-/m1/s1
SMILES	c1cc(c(cc1[C@@H]1[C@@H](CO)Oc2ccc(cc2O1)[C@H]1[C@@H]2CO[C@@H](c3ccc4c(c3)O[C@H](c3ccc(c(c3)O)O)[C@@H](CO)O4)[C@@H]2CO1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	658.21	Volume:	636.605 ? Van der Waals volume.
Dense:	1.034	LogP:	2.471 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.409 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.898 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	43.0
TPSA:	176.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	8.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.162	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.804	Fsp³:	0.333
MCE-18:	150.333 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.986	Fluc inhibitor:	0.51 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.479 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.522	Promiscuous compounds:	0.353

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.244	MDCK Permeability:	-5.097
Pgp-inhibitor:	0.709	Pgp-substrate:	0.002
PAMPA:	0.012 ? 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%):	0.155	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.518	MRP1:	0.904
Plasma Protein Binding (PPB):	89.099%	Volume Distribution (VD):	-0.181
Fu:	13.237% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.657
BSEP inhibitor:	0.752

ADMET: Metabolism

CYP1A2-inhibitor:	0.124	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.97
CYP3A4-inhibitor:	0.046	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.012 ? 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):

11.641

Half-life (T1/2):

2.513

ADMET: Toxicity

hERG Blockers:	0.134	hERG Blockers (10um):	0.377
Human Hepatotoxicity (H-HT):	0.954	Drug-induced Liver Injury (DILI):	0.972
AMES Toxicity:	0.859	Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.106	Skin Sensitization:	1.0
Carcinogencity:	0.09	Eye Corrosion:	0.0
Eye Irritation:	0.851	Respiratory Toxicity:	0.043
Drug-induced Neurotoxicity:	0.055	Ototoxicity:	0.969
Hematotoxicity:	0.06	Drug-induced Nephrotoxicity:	0.242
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.984	Hek293 Cytotoxicity:	0.407
BCF:	1.47 ? 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:	4.287 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.953 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.321 ? 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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36014413]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	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	1
Inhibition	3
Ratio IC50	1

Activity Type	# Activity
Individual protein	3
Single protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1120	Individual protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	<	56.0	%	PMID[32083868]
NPT1120	Individual protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	85.0	%	PMID[32083868]
NPT25169	Single protein	Beta-glucuronidase	Escherichia coli (strain K12)	IC50	=	620.0	nM	PMID[32083868]
NPT3809	Individual protein	Pancreatic alpha-amylase	Sus scrofa	Inhibition	=	21.0	%	PMID[32083868]
NPT25169	Single protein	Beta-glucuronidase	Escherichia coli (strain K12)	Ratio IC50	=	3.5	n.a.	PMID[32083868]

In vitro activity

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

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 NPC488545 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	14581
0.1-0.2	31232
0.2-0.3	3612
0.3-0.4	311
0.4-0.5	97
0.5-0.6	18
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC55793
0.9608	High Similarity	NPC488546
0.65	Remote Similarity	NPC30083
0.6393	Remote Similarity	NPC488544
0.629	Remote Similarity	NPC479108
0.6271	Remote Similarity	NPC72529
0.6066	Remote Similarity	NPC214729
0.5692	Remote Similarity	NPC471664
0.5692	Remote Similarity	NPC471665
0.5686	Remote Similarity	NPC146355
0.5686	Remote Similarity	NPC131747
0.5686	Remote Similarity	NPC257682
0.5606	Remote Similarity	NPC479113
0.55	Remote Similarity	NPC27843
0.55	Remote Similarity	NPC7171
0.5205	Remote Similarity	NPC114119
0.5205	Remote Similarity	NPC471415
0.5185	Remote Similarity	NPC121783
0.5185	Remote Similarity	NPC34902
0.5185	Remote Similarity	NPC18449
0.5077	Remote Similarity	NPC88640
0.5077	Remote Similarity	NPC101153
0.5077	Remote Similarity	NPC193666
0.5077	Remote Similarity	NPC123526
0.5077	Remote Similarity	NPC608725

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3638
0.1-0.2	5379
0.2-0.3	127
0.3-0.4	3
0.4-0.5	3
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