NPASS Compound

Natural Product: NPC5786

Natural Product ID	NPC5786
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4-O-{6-O-[4-O-(6-O-Syringyloyl-Beta-D-Glucopyranosyl)Vanilloyl]-Beta-D-Glucopyranosyl}-2-Methoxy-P-Hydroxyquinone
IUPAC Name	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-methoxy-4-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxycarbonyl]phenoxy]oxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL507011
PubChem CID	24878851
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 98102 0 0 0 0 0 0 0 0999 V2000 11.4396 3.1642 -4.6048 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4170 3.5565 -3.2352 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8402 2.8724 -2.2143 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2243 1.6396 -2.3400 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6411 1.0011 -1.2551 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6838 1.6228 -0.0244 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3069 2.8671 0.0864 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8859 3.5088 -0.9660 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5099 4.7661 -0.8343 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0563 -0.2125 -1.4339 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2180 -0.9219 -0.6194 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6597 -2.0200 0.2251 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4465 -2.6308 0.8931 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3305 -1.7116 1.1826 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2576 -0.4074 0.4530 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5003 0.6647 1.1888 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1313 0.4403 1.3750 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2872 0.3593 0.2367 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8255 0.4761 -0.8715 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8506 0.1470 0.4210 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2792 0.0670 1.6683 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1060 -0.1202 1.8141 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9076 -0.2246 0.6992 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3165 -0.1429 -0.5681 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0478 0.0412 -0.6849 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1448 -0.2556 -1.6808 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6746 -0.2230 -3.0034 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2545 -0.4041 0.8212 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0036 -0.6531 1.9918 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5000 0.6301 2.5404 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9339 0.8085 2.8399 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7248 -0.4348 2.6490 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1968 -1.2366 1.4360 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2605 -0.2914 0.2217 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6394 0.0669 0.0251 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5268 -0.8536 -0.4374 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0343 -2.0188 -0.7233 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9415 -0.6253 -0.6285 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7024 -1.5663 -1.3198 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0383 -1.4888 -1.4755 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7287 -0.4314 -0.9357 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0324 0.5426 -0.2363 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6528 0.4278 -0.0970 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7476 1.5972 0.3012 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2409 2.6828 1.0065 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1262 -0.3254 -1.0836 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7869 -2.4413 -2.1711 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0244 -3.5387 -2.7112 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9157 -1.6152 1.6381 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7146 -1.2385 3.7543 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4367 1.9193 2.1300 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8250 0.8361 3.7984 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5606 0.0758 0.1905 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0739 -2.3242 1.0492 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8489 -3.3578 2.0430 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2913 -3.0128 -0.5115 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3935 3.3298 -5.0132 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6049 2.0883 -4.6458 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1469 3.7596 -5.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2284 1.1940 -3.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2724 1.1976 0.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3203 3.3235 1.0770 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9267 5.4441 -0.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3326 -1.2451 -1.2595 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4102 -1.7038 1.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0839 -3.4359 0.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4039 -1.4479 2.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7951 -0.5792 -0.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7035 1.6780 0.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9408 0.6803 2.2376 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9372 0.1639 2.5190 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5055 -0.1715 2.8321 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4996 0.1072 -1.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3159 -0.9223 -3.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3467 -0.5768 -3.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8317 0.7938 -3.4326 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2217 -1.0994 2.7057 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1424 1.4857 1.9011 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1170 1.1221 3.9267 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7922 -0.2178 2.4009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8938 -2.0594 1.2747 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6992 0.6206 0.4045 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8289 -0.8021 -0.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1576 -2.3983 -1.7614 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1394 1.1993 0.4564 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0902 3.2322 1.5205 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7558 3.4166 0.3284 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4779 2.4109 1.7875 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6396 -1.1871 -0.8656 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6744 -4.2885 -3.1882 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4621 -3.9802 -1.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2553 -3.0969 -3.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1210 -0.7575 4.5311 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4110 2.0184 2.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8811 1.8164 3.9717 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1612 -3.0879 0.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3281 -4.1559 1.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1025 -3.9215 -0.1694 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 23 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 1 0 41 46 1 0 40 47 1 0 47 48 1 0 33 49 1 0 32 50 1 0 31 51 1 0 30 52 1 0 15 53 1 0 14 54 1 0 13 55 1 0 12 56 1 0 8 3 1 0 53 11 1 0 25 20 1 0 49 29 1 0 43 38 1 0 1 57 1 0 1 58 1 0 1 59 1 0 4 60 1 0 6 61 1 0 7 62 1 0 9 63 1 0 11 64 1 6 12 65 1 1 13 66 1 6 14 67 1 1 15 68 1 6 16 69 1 0 16 70 1 0 21 71 1 0 22 72 1 0 25 73 1 0 27 74 1 0 27 75 1 0 27 76 1 0 29 77 1 1 30 78 1 6 31 79 1 1 32 80 1 6 33 81 1 6 34 82 1 0 34 83 1 0 39 84 1 0 43 85 1 0 45 86 1 0 45 87 1 0 45 88 1 0 46 89 1 0 48 90 1 0 48 91 1 0 48 92 1 0 50 93 1 0 51 94 1 0 52 95 1 0 54 96 1 0 55 97 1 0 56 98 1 0 M END

Standard InCHIKey	OCULIFYKQDFJQQ-JRGOIJCHSA-N
Standard InCHI	InChI=1S/C36H42O20/c1-47-20-12-17(6-7-18(20)37)53-35-31(43)29(41)27(39)24(55-35)13-51-33(45)15-5-8-19(21(9-15)48-2)54-36-32(44)30(42)28(40)25(56-36)14-52-34(46)16-10-22(49-3)26(38)23(11-16)50-4/h5-12,24-25,27-32,35-44H,13-14H2,1-4H3/t24-,25-,27-,28-,29+,30+,31-,32-,35-,36-/m1/s1
SMILES	COc1cc(ccc1O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c2ccc(c(c2)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c3cc(c(c(c3)OC)O)OC)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	794.23	Volume:	735.233 ? Van der Waals volume.
Dense:	1.08	LogP:	1.065 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.461 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.79 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	32.0
TPSA:	288.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.093	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.795	Fsp³:	0.444
MCE-18:	125.231 ? 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:	0
Colloidal aggregators:	0.533	Fluc inhibitor:	0.23 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.298 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.616 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.118	Promiscuous compounds:	0.515

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.117	MDCK Permeability:	-5.49
Pgp-inhibitor:	0.27	Pgp-substrate:	0.003
PAMPA:	0.227 ? 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):	0.206
20% Bioavailability (F20%):	0.554	30% Bioavailability (F30%):	0.986
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024	MRP1:	0.01
Plasma Protein Binding (PPB):	84.371%	Volume Distribution (VD):	-0.505
Fu:	16.358% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.745

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.987
HLM stability:	0.746 ? 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):

2.277

Half-life (T1/2):

5.738

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.317
Human Hepatotoxicity (H-HT):	0.083	Drug-induced Liver Injury (DILI):	0.979
AMES Toxicity:	0.913	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	0.993
Carcinogencity:	0.373	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.985
Hematotoxicity:	0.03	Drug-induced Nephrotoxicity:	0.73
Genotoxicity:	0.063	RPMI-8226 Immunitoxicity:	0.427
A549 Cytotoxicity:	0.495	Hek293 Cytotoxicity:	0.527
BCF:	0.318 ? 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:	3.451 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.514 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.081 ? 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
NPO21315	Adina polycephala	Species	Rubiaceae	Eukaryota	bark	n.a.	n.a.	PMID[18303851]
NPO21315	Adina polycephala	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
Inhibition	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	25.2	%	PMID[18303851]

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 NPC5786 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	14615
0.1-0.2	30517
0.2-0.3	3918
0.3-0.4	675
0.4-0.5	103
0.5-0.6	21
0.6-0.7	1
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
0.7887	Intermediate Similarity	NPC102851
0.7857	Intermediate Similarity	NPC197708
0.7361	Intermediate Similarity	NPC327032
0.7183	Intermediate Similarity	NPC119125
0.7123	Intermediate Similarity	NPC311803
0.7051	Intermediate Similarity	NPC658
0.7042	Intermediate Similarity	NPC25389
0.6	Remote Similarity	NPC111785
0.5789	Remote Similarity	NPC472859
0.5761	Remote Similarity	NPC163165
0.5753	Remote Similarity	NPC65833
0.5733	Remote Similarity	NPC37074
0.5696	Remote Similarity	NPC160780
0.5663	Remote Similarity	NPC602634
0.5658	Remote Similarity	NPC166277
0.5658	Remote Similarity	NPC287780
0.5658	Remote Similarity	NPC60982
0.5579	Remote Similarity	NPC316539
0.5529	Remote Similarity	NPC485743
0.5465	Remote Similarity	NPC478797
0.5316	Remote Similarity	NPC1913
0.5286	Remote Similarity	NPC221090
0.5275	Remote Similarity	NPC485745
0.5176	Remote Similarity	NPC485234
0.5116	Remote Similarity	NPC194095
0.5114	Remote Similarity	NPC33298
0.5062	Remote Similarity	NPC215811
0.506	Remote Similarity	NPC36130
0.5057	Remote Similarity	NPC471405

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC5786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4056
0.1-0.2	4939
0.2-0.3	148
0.3-0.4	7
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