NPASS Compound

Natural Product: NPC544511

Natural Product ID	NPC544511
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-dihydroxy-2-[3-methoxy-4-[(2~{S},3~{S},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-3-[(2~{S},3~{R},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5,7-dihydroxy-2-[3-methoxy-4-[(2~{S},3~{S},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-3-[(2~{S},3~{R},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
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 96101 0 0 0 0 0 0 0 0999 V2000 0.2079 2.1189 -1.6238 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5092 1.8867 -1.2576 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0202 0.8810 -0.4257 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2458 -0.0804 0.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7328 -1.0653 0.9943 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9682 -2.1151 1.6130 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2877 -2.4990 1.2930 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0532 -1.9311 0.2790 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0690 -2.3789 -1.0562 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0563 -1.3162 -1.9001 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2633 -0.7852 -2.2517 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7837 0.0091 -1.0694 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0051 0.5613 -1.4549 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5767 1.3256 -0.4634 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7993 0.7565 -0.1290 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4211 1.4466 0.9113 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5797 0.6089 1.3896 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9299 2.7436 0.3230 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7201 2.4658 -0.7912 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7181 3.5389 -0.1138 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0671 4.6833 -0.8280 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7867 2.7313 -0.9863 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5727 3.4282 -1.0229 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3317 -1.6902 -2.7121 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4420 -1.6040 -1.8672 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8233 -3.1123 -2.6714 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8108 -3.3001 -3.6129 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2343 -3.3028 -1.2820 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8651 -4.6368 -1.2072 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9204 -3.5457 1.9894 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0711 -3.9447 1.7522 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2408 -4.1779 3.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8228 -5.2212 3.7183 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1130 -5.6054 3.3854 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0768 -5.8038 4.7142 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2042 -5.3684 4.9909 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9299 -5.9700 5.9938 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7689 -4.3422 4.2805 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0304 -3.7422 3.2716 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5679 -2.7759 2.6061 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1105 -1.0677 1.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9123 -0.1116 0.6091 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3952 0.8586 -0.1999 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1679 1.8025 -0.7915 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5330 2.0150 -0.7143 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7527 3.3046 -0.2395 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9622 3.3641 0.4319 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1757 4.7718 0.9061 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0305 2.8579 -0.4908 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0604 3.8102 -0.5116 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5605 2.6967 -1.9206 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3781 3.9628 -2.5102 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2846 1.8828 -2.0178 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5897 2.2998 -3.1242 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3874 2.5386 -0.7812 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2698 1.2709 -2.1167 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2301 2.9617 -2.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1802 -0.0273 0.0183 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1670 -2.9969 -1.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0680 -0.0117 -3.0447 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9674 -0.7620 -0.2598 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0745 0.7059 -0.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9476 1.3558 0.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6952 1.6782 1.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9535 -0.0322 0.5849 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4243 1.2351 1.7590 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2798 -0.0256 2.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4918 3.3565 1.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4255 1.6014 -1.2082 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1629 3.8213 0.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4421 4.8346 -1.5838 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1529 2.6725 -2.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2017 3.5131 -1.9248 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6290 -1.4165 -3.7623 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -2.2547 -2.0956 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6404 -3.8189 -2.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7254 -2.4569 -4.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0521 -3.1192 -0.5822 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6598 -5.1967 -1.0444 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8899 -5.6334 4.0263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5396 -6.6114 5.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1454 -6.9510 5.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7717 -3.9681 4.4658 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5221 -1.8304 1.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9793 -0.1948 0.8341 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0499 1.3184 -0.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8692 2.6471 1.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5600 5.4997 0.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2248 5.1091 0.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7605 4.8416 1.9430 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4683 1.8842 -0.1686 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6950 3.6430 -1.2638 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4042 2.2192 -2.4723 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6149 3.9390 -3.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5977 0.8223 -2.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6516 2.5198 -2.8812 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 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 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 16 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 11 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 7 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 33 35 1 0 35 36 2 0 36 37 1 0 36 38 1 0 38 39 2 0 39 40 1 0 5 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 43 3 1 0 53 45 1 0 40 6 1 0 28 9 1 0 39 32 1 0 22 14 1 0 1 55 1 0 1 56 1 0 1 57 1 0 4 58 1 0 9 59 1 6 11 60 1 6 12 61 1 0 12 62 1 0 14 63 1 1 16 64 1 1 17 65 1 0 17 66 1 0 17 67 1 0 18 68 1 1 19 69 1 0 20 70 1 1 21 71 1 0 22 72 1 6 23 73 1 0 24 74 1 6 25 75 1 0 26 76 1 6 27 77 1 0 28 78 1 1 29 79 1 0 34 80 1 0 35 81 1 0 37 82 1 0 38 83 1 0 41 84 1 0 42 85 1 0 45 86 1 1 47 87 1 1 48 88 1 0 48 89 1 0 48 90 1 0 49 91 1 1 50 92 1 0 51 93 1 6 52 94 1 0 53 95 1 6 54 96 1 0 M END

Standard InCHIKey	YJJATMIYFDTODI-YPWUYVOYSA-N
Standard InCHI	InChI=1S/C34H42O20/c1-10-20(37)24(41)27(44)32(49-10)48-9-18-22(39)26(43)29(46)34(53-18)54-31-23(40)19-14(36)7-13(35)8-17(19)51-30(31)12-4-5-15(16(6-12)47-3)52-33-28(45)25(42)21(38)11(2)50-33/h4-8,10-11,18,20-22,24-29,32-39,41-46H,9H2,1-3H3/t10-,11-,18-,20+,21+,22+,24+,25+,26-,27-,28+,29-,32-,33+,34+/m1/s1
SMILES	COC1=CC(C2=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@H](C)[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@@H](O)[C@H]3O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[C@@H]1O[C@H](C)[C@H](O)[C@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	770.23	Volume:	699.994 ? Van der Waals volume.
Dense:	1.1	LogP:	0.931 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.468 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.067 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	317.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.35	Fsp³:	0.559
MCE-18:	153.34 ? 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:	0.629	Fluc inhibitor:	0.278 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.664 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.456 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.082	Promiscuous compounds:	0.508

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.539	MDCK Permeability:	-5.165
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
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):	0.996
20% Bioavailability (F20%):	0.954	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.394
Plasma Protein Binding (PPB):	85.057%	Volume Distribution (VD):	-0.117
Fu:	14.102% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.484
OATP1B3 inhibitor:	0.984	BCRP inhibitor:	0.554
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:	0.224
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.979
HLM stability:	0.685 ? 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):

0.738

Half-life (T1/2):

3.78

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.047
Human Hepatotoxicity (H-HT):	0.62	Drug-induced Liver Injury (DILI):	0.983
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.019	Skin Sensitization:	1.0
Carcinogencity:	0.078	Eye Corrosion:	0.0
Eye Irritation:	0.157	Respiratory Toxicity:	0.06
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.959
Hematotoxicity:	0.765	Drug-induced Nephrotoxicity:	0.724
Genotoxicity:	0.937	RPMI-8226 Immunitoxicity:	0.445
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.955
BCF:	0.299 ? 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:	3.143 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.68 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.806 ? 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
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	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 NPC544511 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	14717
0.1-0.2	30851
0.2-0.3	3295
0.3-0.4	532
0.4-0.5	226
0.5-0.6	124
0.6-0.7	58
0.7-0.8	2
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8315	Intermediate Similarity	NPC473327
0.8132	Intermediate Similarity	NPC476472
0.8132	Intermediate Similarity	NPC294815
0.8132	Intermediate Similarity	NPC16194
0.7955	Intermediate Similarity	NPC173582
0.7955	Intermediate Similarity	NPC265885
0.7955	Intermediate Similarity	NPC181465
0.7955	Intermediate Similarity	NPC215710
0.7955	Intermediate Similarity	NPC473438
0.7955	Intermediate Similarity	NPC253788
0.7865	Intermediate Similarity	NPC203259
0.7865	Intermediate Similarity	NPC33054
0.7865	Intermediate Similarity	NPC176740
0.7865	Intermediate Similarity	NPC471725
0.7865	Intermediate Similarity	NPC134532
0.7865	Intermediate Similarity	NPC602582
0.7753	Intermediate Similarity	NPC39834
0.7065	Intermediate Similarity	NPC187379
0.6966	Remote Similarity	NPC219904
0.6947	Remote Similarity	NPC153755
0.6931	Remote Similarity	NPC173837
0.6931	Remote Similarity	NPC477895
0.6915	Remote Similarity	NPC156869
0.69	Remote Similarity	NPC89052
0.6882	Remote Similarity	NPC471079
0.6882	Remote Similarity	NPC609888
0.6842	Remote Similarity	NPC473571
0.6842	Remote Similarity	NPC110941
0.6813	Remote Similarity	NPC223747
0.6809	Remote Similarity	NPC67326
0.6771	Remote Similarity	NPC126784
0.6771	Remote Similarity	NPC241423
0.6701	Remote Similarity	NPC12013
0.6701	Remote Similarity	NPC11432
0.6701	Remote Similarity	NPC477613
0.6667	Remote Similarity	NPC116864
0.6667	Remote Similarity	NPC244776
0.6667	Remote Similarity	NPC189564
0.6667	Remote Similarity	NPC89127
0.6667	Remote Similarity	NPC186816
0.6633	Remote Similarity	NPC122467
0.6629	Remote Similarity	NPC265530
0.6602	Remote Similarity	NPC292019
0.6602	Remote Similarity	NPC202908
0.6591	Remote Similarity	NPC111929
0.6591	Remote Similarity	NPC320283
0.6591	Remote Similarity	NPC41121
0.6569	Remote Similarity	NPC203145
0.6562	Remote Similarity	NPC65563
0.6562	Remote Similarity	NPC470949
0.6517	Remote Similarity	NPC127546
0.6517	Remote Similarity	NPC57625
0.6517	Remote Similarity	NPC173637
0.6517	Remote Similarity	NPC317489
0.6517	Remote Similarity	NPC223424
0.6517	Remote Similarity	NPC600591
0.6442	Remote Similarity	NPC48984
0.6436	Remote Similarity	NPC221342
0.6436	Remote Similarity	NPC476470
0.6404	Remote Similarity	NPC135599
0.6404	Remote Similarity	NPC73855
0.6404	Remote Similarity	NPC113968
0.6404	Remote Similarity	NPC328940
0.6404	Remote Similarity	NPC277174
0.6404	Remote Similarity	NPC606877
0.6373	Remote Similarity	NPC602448
0.6364	Remote Similarity	NPC470443
0.6306	Remote Similarity	NPC192539
0.6129	Remote Similarity	NPC472459
0.6075	Remote Similarity	NPC217520
0.6075	Remote Similarity	NPC303694
0.6071	Remote Similarity	NPC241781
0.6019	Remote Similarity	NPC473073
0.6019	Remote Similarity	NPC471669
0.6	Remote Similarity	NPC129264
0.6	Remote Similarity	NPC120099
0.5963	Remote Similarity	NPC139571
0.5941	Remote Similarity	NPC488073
0.5941	Remote Similarity	NPC488074
0.5914	Remote Similarity	NPC64305
0.59	Remote Similarity	NPC605592
0.5897	Remote Similarity	NPC473554
0.5895	Remote Similarity	NPC175107
0.5893	Remote Similarity	NPC162394
0.5876	Remote Similarity	NPC203050
0.5876	Remote Similarity	NPC225434
0.5876	Remote Similarity	NPC476215
0.5865	Remote Similarity	NPC470447
0.5865	Remote Similarity	NPC85751
0.5865	Remote Similarity	NPC19240
0.5865	Remote Similarity	NPC220173
0.5842	Remote Similarity	NPC204693
0.5825	Remote Similarity	NPC37668
0.5825	Remote Similarity	NPC270448
0.5816	Remote Similarity	NPC95866
0.581	Remote Similarity	NPC287889
0.581	Remote Similarity	NPC470449
0.581	Remote Similarity	NPC470445
0.5789	Remote Similarity	NPC325555
0.5789	Remote Similarity	NPC226304
0.5784	Remote Similarity	NPC470125
0.5784	Remote Similarity	NPC475366
0.5773	Remote Similarity	NPC88023
0.5769	Remote Similarity	NPC142142
0.5755	Remote Similarity	NPC470446
0.5755	Remote Similarity	NPC223426
0.5752	Remote Similarity	NPC156785
0.5752	Remote Similarity	NPC474522
0.5743	Remote Similarity	NPC22062
0.5743	Remote Similarity	NPC473634
0.5743	Remote Similarity	NPC138811
0.5729	Remote Similarity	NPC60735
0.5729	Remote Similarity	NPC26230
0.5701	Remote Similarity	NPC214621
0.5701	Remote Similarity	NPC34267
0.5701	Remote Similarity	NPC81042
0.5684	Remote Similarity	NPC46420
0.5673	Remote Similarity	NPC209296
0.567	Remote Similarity	NPC609478
0.5664	Remote Similarity	NPC480445
0.566	Remote Similarity	NPC292929
0.5644	Remote Similarity	NPC163242
0.5644	Remote Similarity	NPC272068
0.5644	Remote Similarity	NPC67105
0.5638	Remote Similarity	NPC77672
0.5638	Remote Similarity	NPC133671
0.5638	Remote Similarity	NPC135391
0.5638	Remote Similarity	NPC78263
0.5638	Remote Similarity	NPC250069
0.5588	Remote Similarity	NPC155877
0.5579	Remote Similarity	NPC145038
0.5579	Remote Similarity	NPC56077
0.5579	Remote Similarity	NPC281131
0.5579	Remote Similarity	NPC253662
0.5579	Remote Similarity	NPC179950
0.5579	Remote Similarity	NPC88789
0.5579	Remote Similarity	NPC491374
0.5567	Remote Similarity	NPC611303
0.5566	Remote Similarity	NPC76831
0.5565	Remote Similarity	NPC480444
0.5546	Remote Similarity	NPC487499
0.5529	Remote Similarity	NPC603596
0.5521	Remote Similarity	NPC305811
0.5521	Remote Similarity	NPC271692
0.5495	Remote Similarity	NPC25523
0.549	Remote Similarity	NPC227508
0.5474	Remote Similarity	NPC19388
0.5474	Remote Similarity	NPC240431
0.5474	Remote Similarity	NPC55786
0.5455	Remote Similarity	NPC209023
0.5455	Remote Similarity	NPC309025
0.544	Remote Similarity	NPC487500
0.5439	Remote Similarity	NPC488734
0.5439	Remote Similarity	NPC488735
0.5439	Remote Similarity	NPC488739
0.5439	Remote Similarity	NPC488732
0.5439	Remote Similarity	NPC488738
0.5417	Remote Similarity	NPC158674
0.5413	Remote Similarity	NPC470455
0.5408	Remote Similarity	NPC159579
0.5405	Remote Similarity	NPC219043
0.5397	Remote Similarity	NPC487501
0.5392	Remote Similarity	NPC139320
0.5376	Remote Similarity	NPC54802
0.5376	Remote Similarity	NPC197304
0.5366	Remote Similarity	NPC487502
0.5361	Remote Similarity	NPC27640
0.5357	Remote Similarity	NPC480441
0.5345	Remote Similarity	NPC488740
0.5345	Remote Similarity	NPC488736
0.5345	Remote Similarity	NPC488733
0.534	Remote Similarity	NPC44931
0.534	Remote Similarity	NPC471748
0.5333	Remote Similarity	NPC296018
0.5333	Remote Similarity	NPC154741
0.5319	Remote Similarity	NPC288084
0.5319	Remote Similarity	NPC276222
0.5319	Remote Similarity	NPC274618
0.5319	Remote Similarity	NPC118284
0.5319	Remote Similarity	NPC608147
0.5315	Remote Similarity	NPC470451
0.5312	Remote Similarity	NPC249281
0.5306	Remote Similarity	NPC216496
0.5294	Remote Similarity	NPC278419
0.5294	Remote Similarity	NPC179198
0.5288	Remote Similarity	NPC210073
0.5263	Remote Similarity	NPC67037
0.5263	Remote Similarity	NPC255615
0.5254	Remote Similarity	NPC488737
0.5253	Remote Similarity	NPC182121
0.5253	Remote Similarity	NPC129217
0.5248	Remote Similarity	NPC276377
0.5246	Remote Similarity	NPC275977
0.5246	Remote Similarity	NPC483159
0.5246	Remote Similarity	NPC483160
0.5243	Remote Similarity	NPC29958
0.5225	Remote Similarity	NPC121703
0.5204	Remote Similarity	NPC52550
0.5196	Remote Similarity	NPC265115
0.5192	Remote Similarity	NPC470405

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC544511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4730
0.1-0.2	4357
0.2-0.3	50
0.3-0.4	7
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
0.7-0.8	2
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
0.7865	Intermediate Similarity	NPD6797	Phase 2
0.7071	Intermediate Similarity	NPD7808	Phase 3
0.6019	Remote Similarity	NPD7251	Phase 2
0.5673	Remote Similarity	NPD7054	Phase 4
0.5089	Remote Similarity	NPD7472	Pre-clinical

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