NPASS Compound

Natural Product: NPC541276

Natural Product ID	NPC541276
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{S},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 92 97 0 0 0 0 0 0 0 0999 V2000 -9.3369 1.6085 -1.0013 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4646 1.2351 0.1888 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9308 -0.0404 0.0290 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0237 -0.3656 1.0235 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7802 0.1855 0.7494 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8286 -0.7840 0.4500 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4826 -0.1360 0.1680 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5632 -1.1066 -0.1406 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6954 -0.7545 -1.1400 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6551 -1.6744 -1.3351 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6656 -1.3977 -0.9330 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1696 -1.8462 0.2503 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4475 -2.6640 1.2215 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7087 -3.3472 1.0171 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 -4.0724 2.0170 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 -4.1280 3.2909 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4754 -4.8477 4.2932 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3376 -3.4399 3.5117 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9675 -2.7284 2.5188 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4291 -1.5023 0.5286 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2002 -0.7884 -0.2294 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5010 -0.4828 0.1495 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3449 0.2690 -0.6245 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6006 0.5100 -0.1602 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6331 1.2421 -0.7229 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6991 0.3465 -0.9494 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8846 1.0514 -1.1283 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8832 0.2378 -1.8766 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5583 -0.9088 -2.2374 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1412 0.6986 -2.1835 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3888 1.3777 0.2788 C 0 0 1 0 0 0 0 0 0 0 0 0 11.4193 2.3083 0.2314 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2517 1.9176 1.0844 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7969 0.9517 2.0023 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0571 2.3127 0.2692 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3319 3.4675 -0.4279 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8732 0.7361 -1.8270 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5797 0.4515 -2.2399 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1054 0.9296 -3.4649 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7602 -0.3036 -1.4419 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4663 -0.6228 -1.7867 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0439 -0.2014 -2.8706 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5591 -0.5507 -2.3827 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8839 -0.6565 -3.5647 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2595 0.7835 -2.1776 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3843 0.8944 -2.9919 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5488 1.0363 -0.7397 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7781 2.1170 -0.2490 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5178 -0.0760 2.4002 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3610 -1.1815 3.2231 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0068 0.2018 2.3249 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4904 0.5108 3.5940 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3007 1.3727 1.4145 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9466 2.5464 2.0733 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9548 1.0623 -1.8908 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2730 2.6991 -1.1754 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3947 1.3176 -0.8318 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6243 1.9423 0.2346 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8963 -1.4860 0.9360 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6830 -1.5021 1.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2083 -1.3629 -0.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1621 0.2704 1.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1929 0.2232 -0.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1446 -3.3585 0.0393 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2829 -4.6036 1.8045 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2645 -4.6085 5.2754 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7662 -3.4726 4.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8842 -2.1984 2.7213 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8185 -0.8853 1.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3130 1.7032 -1.6646 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6818 2.0046 -1.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8693 0.1744 -2.6321 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7665 0.4100 0.7221 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2396 1.9243 -0.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6083 2.7700 1.6765 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8988 1.2565 2.9373 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2059 2.5338 0.9755 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5787 4.1160 -0.3501 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5069 1.3260 -2.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5649 0.6061 -4.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2978 -1.3914 -2.3599 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9018 -1.5793 -3.9112 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5316 1.5584 -2.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6673 -0.0530 -3.1977 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6089 1.4284 -0.6890 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6483 2.7316 -1.0194 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0563 0.8388 2.8294 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7341 -1.9566 2.7273 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5438 -0.7246 1.9896 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9483 1.2431 4.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3874 1.4218 1.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6567 2.9283 2.6160 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 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 2 0 12 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 23 37 2 0 37 38 1 0 38 39 1 0 38 40 2 0 40 41 1 0 41 42 2 0 9 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 4 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 53 2 1 0 47 7 1 0 41 11 1 0 19 13 1 0 40 21 1 0 35 25 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 1 4 59 1 1 6 60 1 0 6 61 1 0 7 62 1 1 9 63 1 1 14 64 1 0 15 65 1 0 17 66 1 0 18 67 1 0 19 68 1 0 22 69 1 0 25 70 1 6 27 71 1 6 30 72 1 0 31 73 1 1 32 74 1 0 33 75 1 1 34 76 1 0 35 77 1 1 36 78 1 0 37 79 1 0 39 80 1 0 43 81 1 6 44 82 1 0 45 83 1 6 46 84 1 0 47 85 1 6 48 86 1 0 49 87 1 1 50 88 1 0 51 89 1 6 52 90 1 0 53 91 1 6 54 92 1 0 M END

Standard InCHIKey	AVISVHAJGJXBKQ-QPCKMWDZSA-N
Standard InCHI	InChI=1S/C33H38O21/c1-9-17(36)20(39)24(43)31(49-9)48-8-15-18(37)21(40)25(44)33(52-15)53-28-19(38)16-13(35)6-12(7-14(16)51-27(28)10-2-4-11(34)5-3-10)50-32-26(45)22(41)23(42)29(54-32)30(46)47/h2-7,9,15,17-18,20-26,29,31-37,39-45H,8H2,1H3,(H,46,47)/t9-,15+,17-,18+,20-,21-,22-,23-,24+,25+,26+,29-,31+,32+,33-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(C4=CC=C(O)C=C4)OC4=CC(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O)=CC(O)=C4C3=O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	770.19	Volume:	688.852 ? Van der Waals volume.
Dense:	1.118	LogP:	0.045 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.045 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.078 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	37.0
TPSA:	345.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.099	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.361	Fsp³:	0.515
MCE-18:	154.8 ? 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:	0.452	Fluc inhibitor:	0.348 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.714 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.639 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.213	Promiscuous compounds:	0.478

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.73	MDCK Permeability:	-4.852
Pgp-inhibitor:	0.0	Pgp-substrate:	0.959
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):	0.705
20% Bioavailability (F20%):	0.02	30% Bioavailability (F30%):	0.884
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.072
Plasma Protein Binding (PPB):	71.271%	Volume Distribution (VD):	-0.209
Fu:	25.142% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.821
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.021
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.892
HLM stability:	0.001 ? 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):

0.338

Half-life (T1/2):

7.054

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.023
Human Hepatotoxicity (H-HT):	0.55	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.612	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	0.994
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.063	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.991
Hematotoxicity:	0.042	Drug-induced Nephrotoxicity:	0.891
Genotoxicity:	0.821	RPMI-8226 Immunitoxicity:	0.112
A549 Cytotoxicity:	0.068	Hek293 Cytotoxicity:	0.079
BCF:	0.303 ? 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:	2.828 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.566 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.563 ? 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
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25126881]
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO45185	Macroptilium spp.	Genus	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO45945	Vigna peduncularis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO51089	Vigna adenantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11984	Tulipa gesneriana	Species	Liliaceae	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

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

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 NPC541276 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	21467
0.1-0.2	25393
0.2-0.3	2243
0.3-0.4	344
0.4-0.5	257
0.5-0.6	96
0.6-0.7	50
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8261	Intermediate Similarity	NPC186816
0.6981	Remote Similarity	NPC25523
0.6939	Remote Similarity	NPC173582
0.6939	Remote Similarity	NPC265885
0.6939	Remote Similarity	NPC181465
0.6939	Remote Similarity	NPC215710
0.6939	Remote Similarity	NPC473438
0.6939	Remote Similarity	NPC253788
0.6863	Remote Similarity	NPC142142
0.6857	Remote Similarity	NPC121703
0.6848	Remote Similarity	NPC249281
0.6768	Remote Similarity	NPC44931
0.6702	Remote Similarity	NPC46420
0.6701	Remote Similarity	NPC276377
0.66	Remote Similarity	NPC67105
0.6535	Remote Similarity	NPC203259
0.6535	Remote Similarity	NPC65563
0.6535	Remote Similarity	NPC33054
0.6535	Remote Similarity	NPC210073
0.6535	Remote Similarity	NPC470949
0.6535	Remote Similarity	NPC176740
0.6535	Remote Similarity	NPC471725
0.6535	Remote Similarity	NPC134532
0.6535	Remote Similarity	NPC602582
0.6514	Remote Similarity	NPC480441
0.6505	Remote Similarity	NPC470443
0.6491	Remote Similarity	NPC209550
0.6471	Remote Similarity	NPC473571
0.6471	Remote Similarity	NPC110941
0.6429	Remote Similarity	NPC116458
0.6429	Remote Similarity	NPC246943
0.6373	Remote Similarity	NPC150164
0.6321	Remote Similarity	NPC473073
0.6286	Remote Similarity	NPC32641
0.6286	Remote Similarity	NPC256188
0.6186	Remote Similarity	NPC271692
0.6147	Remote Similarity	NPC14187
0.6132	Remote Similarity	NPC72016
0.6132	Remote Similarity	NPC35119
0.6117	Remote Similarity	NPC39834
0.6117	Remote Similarity	NPC227508
0.6095	Remote Similarity	NPC126784
0.6095	Remote Similarity	NPC241423
0.6095	Remote Similarity	NPC64051
0.6082	Remote Similarity	NPC297987
0.6061	Remote Similarity	NPC282169
0.6019	Remote Similarity	NPC476472
0.6019	Remote Similarity	NPC294815
0.6019	Remote Similarity	NPC16194
0.6019	Remote Similarity	NPC471079
0.6018	Remote Similarity	NPC277532
0.5943	Remote Similarity	NPC240306
0.5941	Remote Similarity	NPC605784
0.5932	Remote Similarity	NPC138990
0.5905	Remote Similarity	NPC22062
0.5905	Remote Similarity	NPC473634
0.5905	Remote Similarity	NPC303913
0.5905	Remote Similarity	NPC138811
0.5888	Remote Similarity	NPC12013
0.5888	Remote Similarity	NPC11432
0.5888	Remote Similarity	NPC477613
0.5882	Remote Similarity	NPC175429
0.5833	Remote Similarity	NPC209296
0.5833	Remote Similarity	NPC229409
0.5833	Remote Similarity	NPC473327
0.5758	Remote Similarity	NPC158674
0.5755	Remote Similarity	NPC156869
0.5752	Remote Similarity	NPC189564
0.5743	Remote Similarity	NPC235260
0.5743	Remote Similarity	NPC155763
0.5743	Remote Similarity	NPC20505
0.5678	Remote Similarity	NPC480445
0.5676	Remote Similarity	NPC101636
0.5676	Remote Similarity	NPC221342
0.5676	Remote Similarity	NPC476470
0.5664	Remote Similarity	NPC203145
0.566	Remote Similarity	NPC67326
0.5648	Remote Similarity	NPC64425
0.5636	Remote Similarity	NPC486577
0.5625	Remote Similarity	NPC602448
0.56	Remote Similarity	NPC136042
0.5588	Remote Similarity	NPC611303
0.5556	Remote Similarity	NPC111929
0.5556	Remote Similarity	NPC320283
0.5556	Remote Similarity	NPC41121
0.5545	Remote Similarity	NPC122467
0.5524	Remote Similarity	NPC116864
0.5524	Remote Similarity	NPC244776
0.55	Remote Similarity	NPC108831
0.55	Remote Similarity	NPC182634
0.5455	Remote Similarity	NPC480444
0.5446	Remote Similarity	NPC89127
0.5431	Remote Similarity	NPC292019
0.5431	Remote Similarity	NPC202908
0.54	Remote Similarity	NPC331652
0.5398	Remote Similarity	NPC470449
0.537	Remote Similarity	NPC275454
0.5364	Remote Similarity	NPC46202
0.5364	Remote Similarity	NPC488073
0.5364	Remote Similarity	NPC488074
0.5347	Remote Similarity	NPC289667
0.5347	Remote Similarity	NPC238376
0.534	Remote Similarity	NPC138927
0.5327	Remote Similarity	NPC251417
0.5315	Remote Similarity	NPC65711
0.531	Remote Similarity	NPC470447
0.5276	Remote Similarity	NPC483159
0.5276	Remote Similarity	NPC483160
0.5273	Remote Similarity	NPC129264
0.5263	Remote Similarity	NPC298171
0.5243	Remote Similarity	NPC84362
0.5238	Remote Similarity	NPC608742
0.5238	Remote Similarity	NPC610187
0.5196	Remote Similarity	NPC127546
0.5196	Remote Similarity	NPC57625
0.5196	Remote Similarity	NPC19709
0.5196	Remote Similarity	NPC173637
0.5196	Remote Similarity	NPC317489
0.5196	Remote Similarity	NPC223424
0.5196	Remote Similarity	NPC600591
0.5182	Remote Similarity	NPC479405
0.5175	Remote Similarity	NPC85751
0.5175	Remote Similarity	NPC19240
0.5164	Remote Similarity	NPC298666
0.514	Remote Similarity	NPC476215
0.5138	Remote Similarity	NPC187379
0.5135	Remote Similarity	NPC479404
0.5133	Remote Similarity	NPC270448
0.5133	Remote Similarity	NPC606657
0.5128	Remote Similarity	NPC89052
0.5126	Remote Similarity	NPC303694
0.512	Remote Similarity	NPC192539
0.5096	Remote Similarity	NPC27640
0.5089	Remote Similarity	NPC470125
0.5089	Remote Similarity	NPC153755
0.5088	Remote Similarity	NPC270675
0.5088	Remote Similarity	NPC195685
0.5086	Remote Similarity	NPC470446
0.5086	Remote Similarity	NPC253685
0.5043	Remote Similarity	NPC80068
0.5043	Remote Similarity	NPC470455
0.5043	Remote Similarity	NPC214621
0.5043	Remote Similarity	NPC34267
0.5043	Remote Similarity	NPC471669
0.5042	Remote Similarity	NPC173837
0.504	Remote Similarity	NPC241781
0.5039	Remote Similarity	NPC473554

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC541276 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4689
0.1-0.2	4404
0.2-0.3	48
0.3-0.4	2
0.4-0.5	3
0.5-0.6	1
0.6-0.7	2
0.7-0.8	1
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
0.7129	Intermediate Similarity	NPD7251	Phase 2
0.6535	Remote Similarity	NPD6797	Phase 2
0.6389	Remote Similarity	NPD7808	Phase 3
0.5833	Remote Similarity	NPD7054	Phase 4

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