NPASS Compound

Natural Product: NPC578374

Natural Product ID	NPC578374
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{S},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-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{S},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 -2.4188 5.3518 -0.2294 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 5.8209 0.6220 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2598 5.1419 0.8571 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0464 3.8990 0.2862 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2070 3.2184 0.5192 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5458 1.9223 -0.0264 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6358 1.0941 -0.5710 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7259 1.2969 -0.6835 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5822 0.6959 0.2761 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5750 -0.0603 -0.3511 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9115 -1.1067 0.5012 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1324 -1.8579 0.0047 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2394 -1.0383 -0.0935 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3216 -1.7727 -0.5386 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7997 -1.3461 -1.7637 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8791 -0.5067 -1.7144 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5823 0.8405 -1.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1122 -1.1277 -1.0932 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7515 -0.1736 -0.2938 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6848 -2.2672 -0.2106 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6856 -2.6398 0.6857 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4268 -1.8320 0.5130 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0956 -2.7025 1.5443 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1381 -0.5965 1.9213 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2469 -1.1921 2.5147 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3893 0.9046 1.9033 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5470 1.1391 1.2026 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1921 1.6299 1.2756 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2440 1.8100 2.3182 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0980 -0.1357 -1.0766 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2896 -0.9606 -1.6081 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4306 -0.5083 -1.0247 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8784 -1.7072 -1.5149 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9535 -2.5713 -2.0853 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2120 -2.0304 -1.4360 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0779 -1.1431 -0.8647 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3987 -1.4006 -0.7563 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1696 -2.4765 -1.1319 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6787 -3.0704 0.0218 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5523 -2.2239 0.6981 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0010 -2.7753 2.0101 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7371 -1.8409 -0.1802 C 0 0 2 0 0 0 0 0 0 0 0 0 10.6692 -1.1009 0.5087 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2610 -1.1768 -1.4395 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7191 0.0737 -1.2155 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2734 -2.1294 -2.1071 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9864 -3.2678 -2.4737 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6033 0.0498 -0.3822 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2751 0.4189 -0.4385 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 1.5540 0.0230 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1055 3.8578 1.3930 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8272 5.0725 1.9632 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6586 5.7477 1.7232 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3678 6.9762 2.2957 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2103 4.7557 0.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9926 6.2306 -0.6806 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9556 4.8218 -1.0788 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6797 3.4610 -0.3941 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9585 -0.0229 0.8915 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0419 -1.7894 0.5461 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9313 -2.3212 -0.9821 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3170 -2.7067 0.7026 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9904 -2.8204 -0.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1624 -0.3010 -2.7893 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5485 1.6623 -1.8730 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3675 1.1625 -0.3871 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6340 0.8752 -0.5656 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8312 -1.4819 -1.8370 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3406 -0.6038 0.3541 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4064 -3.1105 -0.8916 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7011 -3.6452 0.7229 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6266 -0.7935 0.8977 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8539 -3.2024 1.8912 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2633 -0.8082 2.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0461 -2.1278 2.7331 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4615 1.2291 2.9635 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8819 2.0369 1.4149 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4821 2.5910 0.8595 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0702 0.9364 2.7415 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0020 -3.5752 -1.9827 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5692 -3.0030 -1.8346 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5440 -3.2401 -1.6259 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9935 -1.2843 0.8898 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2258 -1.9683 2.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2848 -3.4704 2.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9473 -3.3452 1.8462 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2452 -2.7921 -0.5008 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1489 -0.5237 -0.1383 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1224 -1.1003 -2.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4258 0.7698 -1.3830 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9157 -1.6434 -3.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5781 -4.0768 -2.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2856 0.7784 0.0820 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0329 3.3200 1.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5497 5.5367 2.6371 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7442 7.8134 1.8365 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 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 36 48 1 0 48 49 2 0 49 50 1 0 5 51 2 0 51 52 1 0 52 53 2 0 53 54 1 0 53 3 1 0 50 6 1 0 28 9 1 0 49 32 1 0 22 14 1 0 46 38 1 0 1 55 1 0 1 56 1 0 1 57 1 0 4 58 1 0 9 59 1 1 11 60 1 1 12 61 1 0 12 62 1 0 14 63 1 6 16 64 1 6 17 65 1 0 17 66 1 0 17 67 1 0 18 68 1 6 19 69 1 0 20 70 1 6 21 71 1 0 22 72 1 1 23 73 1 0 24 74 1 1 25 75 1 0 26 76 1 1 27 77 1 0 28 78 1 6 29 79 1 0 34 80 1 0 35 81 1 0 38 82 1 6 40 83 1 1 41 84 1 0 41 85 1 0 41 86 1 0 42 87 1 6 43 88 1 0 44 89 1 6 45 90 1 0 46 91 1 6 47 92 1 0 48 93 1 0 51 94 1 0 52 95 1 0 54 96 1 0 M END

Standard InCHIKey	VXNWHRNUCPQFIN-UBOYIZNTSA-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)19-15(36)7-13(51-33-28(45)25(42)21(38)11(2)50-33)8-17(19)52-30(31)12-4-5-14(35)16(6-12)47-3/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@@H]4O[C@@H](C)[C@H](O)[C@H](O)[C@H]4O)C=C3O2)=CC=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	770.23	Volume:	699.994 ? Van der Waals volume.
Dense:	1.1	LogP:	0.81 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.3 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.037 ? 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:	5.361	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:	1	PAINS Alert:	0
Colloidal aggregators:	0.632	Fluc inhibitor:	0.294 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.701 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.556 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.092	Promiscuous compounds:	0.497

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.511	MDCK Permeability:	-5.245
Pgp-inhibitor:	0.0	Pgp-substrate:	0.99
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):	0.997
20% Bioavailability (F20%):	0.574	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.238
Plasma Protein Binding (PPB):	82.44%	Volume Distribution (VD):	-0.146
Fu:	18.376% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.419
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:	0.931
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.402
HLM stability:	0.42 ? 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):

0.902

Half-life (T1/2):

4.426

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.061
Human Hepatotoxicity (H-HT):	0.731	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	1.0
Carcinogencity:	0.039	Eye Corrosion:	0.0
Eye Irritation:	0.024	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.983
Hematotoxicity:	0.601	Drug-induced Nephrotoxicity:	0.9
Genotoxicity:	0.966	RPMI-8226 Immunitoxicity:	0.51
A549 Cytotoxicity:	0.99	Hek293 Cytotoxicity:	0.805
BCF:	0.377 ? 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:	3.009 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.565 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.722 ? 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
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50070a031]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO49776	Lilium cordatum	Genus	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54208	Cassia italica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23656	Typha latifolia	Species	Typhaceae	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 NPC578374 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	21249
0.1-0.2	25005
0.2-0.3	2650
0.3-0.4	485
0.4-0.5	272
0.5-0.6	125
0.6-0.7	54
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
0.8391	Intermediate Similarity	NPC186816
0.8132	Intermediate Similarity	NPC476472
0.8132	Intermediate Similarity	NPC294815
0.8132	Intermediate Similarity	NPC16194
0.7234	Intermediate Similarity	NPC470443
0.7126	Intermediate Similarity	NPC46420
0.7126	Intermediate Similarity	NPC271692
0.6989	Remote Similarity	NPC67105
0.6979	Remote Similarity	NPC209296
0.6966	Remote Similarity	NPC611303
0.6947	Remote Similarity	NPC126784
0.6947	Remote Similarity	NPC241423
0.6915	Remote Similarity	NPC210073
0.6907	Remote Similarity	NPC142142
0.6897	Remote Similarity	NPC249281
0.6842	Remote Similarity	NPC473571
0.6842	Remote Similarity	NPC110941
0.6813	Remote Similarity	NPC223747
0.6809	Remote Similarity	NPC173582
0.6809	Remote Similarity	NPC44931
0.6809	Remote Similarity	NPC265885
0.6809	Remote Similarity	NPC181465
0.6809	Remote Similarity	NPC215710
0.6809	Remote Similarity	NPC473438
0.6809	Remote Similarity	NPC253788
0.6804	Remote Similarity	NPC473327
0.6771	Remote Similarity	NPC153755
0.6739	Remote Similarity	NPC276377
0.6737	Remote Similarity	NPC22062
0.6737	Remote Similarity	NPC203259
0.6737	Remote Similarity	NPC473634
0.6737	Remote Similarity	NPC33054
0.6737	Remote Similarity	NPC176740
0.6737	Remote Similarity	NPC471725
0.6737	Remote Similarity	NPC134532
0.6737	Remote Similarity	NPC138811
0.6737	Remote Similarity	NPC602582
0.6733	Remote Similarity	NPC89052
0.6699	Remote Similarity	NPC480441
0.6699	Remote Similarity	NPC25523
0.6629	Remote Similarity	NPC158674
0.6602	Remote Similarity	NPC173837
0.65	Remote Similarity	NPC473073
0.6458	Remote Similarity	NPC227508
0.6452	Remote Similarity	NPC116458
0.6452	Remote Similarity	NPC246943
0.6452	Remote Similarity	NPC605784
0.6408	Remote Similarity	NPC121703
0.6392	Remote Similarity	NPC65563
0.6392	Remote Similarity	NPC470949
0.6392	Remote Similarity	NPC150164
0.63	Remote Similarity	NPC606657
0.6289	Remote Similarity	NPC39834
0.625	Remote Similarity	NPC251417
0.6139	Remote Similarity	NPC32641
0.6139	Remote Similarity	NPC256188
0.6139	Remote Similarity	NPC72016
0.61	Remote Similarity	NPC488073
0.6078	Remote Similarity	NPC486577
0.6018	Remote Similarity	NPC192539
0.6	Remote Similarity	NPC14187
0.598	Remote Similarity	NPC35119
0.5941	Remote Similarity	NPC240306
0.5941	Remote Similarity	NPC488074
0.5929	Remote Similarity	NPC209550
0.5926	Remote Similarity	NPC217520
0.5914	Remote Similarity	NPC297987
0.5914	Remote Similarity	NPC136042
0.59	Remote Similarity	NPC303913
0.59	Remote Similarity	NPC156869
0.5876	Remote Similarity	NPC203050
0.5876	Remote Similarity	NPC488072
0.5876	Remote Similarity	NPC225434
0.5872	Remote Similarity	NPC277532
0.5859	Remote Similarity	NPC471079
0.5851	Remote Similarity	NPC84362
0.5851	Remote Similarity	NPC27640
0.5833	Remote Similarity	NPC78326
0.5818	Remote Similarity	NPC139571
0.5806	Remote Similarity	NPC238376
0.58	Remote Similarity	NPC67326
0.5789	Remote Similarity	NPC59534
0.5773	Remote Similarity	NPC311830
0.5755	Remote Similarity	NPC470446
0.5714	Remote Similarity	NPC195257
0.5714	Remote Similarity	NPC220173
0.57	Remote Similarity	NPC609888
0.5686	Remote Similarity	NPC204693
0.5684	Remote Similarity	NPC305811
0.5673	Remote Similarity	NPC473623
0.567	Remote Similarity	NPC101026
0.567	Remote Similarity	NPC488077
0.566	Remote Similarity	NPC101636
0.566	Remote Similarity	NPC470449
0.566	Remote Similarity	NPC470445
0.5644	Remote Similarity	NPC275454
0.5638	Remote Similarity	NPC289667
0.5638	Remote Similarity	NPC108831
0.5638	Remote Similarity	NPC19709
0.5638	Remote Similarity	NPC182634
0.5619	Remote Similarity	NPC488089
0.5603	Remote Similarity	NPC175429
0.5596	Remote Similarity	NPC189564
0.5577	Remote Similarity	NPC12013
0.5577	Remote Similarity	NPC65711
0.5577	Remote Similarity	NPC11432
0.5577	Remote Similarity	NPC477613
0.5567	Remote Similarity	NPC219904
0.5566	Remote Similarity	NPC470447
0.5565	Remote Similarity	NPC488079
0.5556	Remote Similarity	NPC601586
0.5545	Remote Similarity	NPC292019
0.5545	Remote Similarity	NPC202908
0.5532	Remote Similarity	NPC111929
0.5532	Remote Similarity	NPC320283
0.5532	Remote Similarity	NPC331652
0.5532	Remote Similarity	NPC41121
0.5524	Remote Similarity	NPC122467
0.5517	Remote Similarity	NPC138990
0.5505	Remote Similarity	NPC203145
0.5505	Remote Similarity	NPC11468
0.55	Remote Similarity	NPC116864
0.55	Remote Similarity	NPC244776
0.55	Remote Similarity	NPC265115
0.5474	Remote Similarity	NPC127546
0.5474	Remote Similarity	NPC57625
0.5474	Remote Similarity	NPC173637
0.5474	Remote Similarity	NPC317489
0.5474	Remote Similarity	NPC223424
0.5474	Remote Similarity	NPC600591
0.5463	Remote Similarity	NPC135358
0.5455	Remote Similarity	NPC473072
0.5421	Remote Similarity	NPC89127
0.5417	Remote Similarity	NPC265530
0.5392	Remote Similarity	NPC187379
0.5391	Remote Similarity	NPC198199
0.5377	Remote Similarity	NPC229409
0.537	Remote Similarity	NPC221342
0.537	Remote Similarity	NPC476470
0.5361	Remote Similarity	NPC349108
0.5354	Remote Similarity	NPC601144
0.5333	Remote Similarity	NPC46202
0.5333	Remote Similarity	NPC64425
0.5333	Remote Similarity	NPC475366
0.5333	Remote Similarity	NPC64051
0.5321	Remote Similarity	NPC602448
0.53	Remote Similarity	NPC206123
0.5283	Remote Similarity	NPC483414
0.5283	Remote Similarity	NPC483415
0.5273	Remote Similarity	NPC470455
0.5268	Remote Similarity	NPC480796
0.5268	Remote Similarity	NPC472993
0.5254	Remote Similarity	NPC120952
0.5243	Remote Similarity	NPC480466
0.5234	Remote Similarity	NPC483416
0.5229	Remote Similarity	NPC298171
0.5221	Remote Similarity	NPC473644
0.5208	Remote Similarity	NPC473043
0.5179	Remote Similarity	NPC470451
0.5175	Remote Similarity	NPC311850
0.5169	Remote Similarity	NPC470720
0.5149	Remote Similarity	NPC99957
0.5143	Remote Similarity	NPC479405
0.5133	Remote Similarity	NPC219043
0.5133	Remote Similarity	NPC477895
0.5126	Remote Similarity	NPC241781
0.5122	Remote Similarity	NPC473554
0.5098	Remote Similarity	NPC355481
0.5094	Remote Similarity	NPC479404
0.5088	Remote Similarity	NPC303694
0.5085	Remote Similarity	NPC470717
0.5052	Remote Similarity	NPC135599
0.5052	Remote Similarity	NPC73855
0.5052	Remote Similarity	NPC113968
0.5052	Remote Similarity	NPC328940
0.5052	Remote Similarity	NPC277174
0.5052	Remote Similarity	NPC606877
0.505	Remote Similarity	NPC181616
0.505	Remote Similarity	NPC606560
0.5046	Remote Similarity	NPC270675
0.5046	Remote Similarity	NPC195685
0.5045	Remote Similarity	NPC470450
0.5044	Remote Similarity	NPC470416
0.5043	Remote Similarity	NPC68592
0.5043	Remote Similarity	NPC295625
0.5042	Remote Similarity	NPC488078

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC578374 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5522
0.1-0.2	3578
0.2-0.3	41
0.3-0.4	2
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
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
0.7553	Intermediate Similarity	NPD7251	Phase 2
0.7245	Intermediate Similarity	NPD7808	Phase 3
0.6979	Remote Similarity	NPD7054	Phase 4
0.6737	Remote Similarity	NPD6797	Phase 2
0.5505	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