NPASS Compound

Natural Product: NPC32572

Natural Product ID	NPC32572
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OGYXOOJUJQIDOX-XKRLVHJLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 85 89 0 0 0 0 0 0 0 0999 V2000 0.9460 -1.4531 -4.0565 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0224 -0.5841 -3.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4477 -0.5516 -2.2878 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9313 -1.3755 -1.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4594 -0.5320 -0.0445 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4373 0.1013 0.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0137 0.8793 1.7723 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6794 1.0291 2.0629 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2640 0.3890 1.2886 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 0.5297 1.5660 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9418 1.2461 2.5327 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5007 -0.1516 0.7375 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1119 -0.9230 -0.2882 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9941 -1.6657 -1.1692 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3032 -1.9570 -0.9329 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1197 -2.6384 -1.8226 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6255 -3.0686 -3.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3024 -2.7938 -3.3041 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5117 -2.1156 -2.4064 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4192 -3.7498 -3.9317 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7835 -1.0212 -0.5172 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1172 -0.4165 0.2045 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8319 0.0535 1.0681 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5967 1.1450 0.5687 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0780 2.0980 1.6371 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7308 1.2973 2.7403 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8341 0.4837 2.1168 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8990 0.7458 0.6407 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8172 -0.3633 0.0710 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7465 0.7046 -0.0688 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0472 0.9322 2.7193 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8182 0.3814 3.3000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2082 3.0616 2.0354 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2280 1.8061 3.1144 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7591 -0.0884 0.3797 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8703 0.4336 1.0170 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7158 -0.7756 1.4412 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0870 -0.4004 1.8889 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6826 0.5250 0.8281 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7600 1.6972 0.6744 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3539 2.7550 -0.2021 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5298 3.1962 0.4090 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5738 1.2195 0.0966 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9555 0.9134 1.2128 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8433 -1.5710 1.9600 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -1.5066 2.3637 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6536 0.3420 -4.5595 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8104 -2.3876 -3.4989 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0087 -0.8846 -4.1429 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1936 -1.7685 -5.1138 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2668 0.1626 -2.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0898 -1.9865 -1.5572 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6838 -2.0992 -0.7971 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7089 1.3920 2.3970 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7428 -1.6853 0.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1619 -2.8558 -1.6051 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9353 -3.1412 -4.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4850 -1.9020 -2.6081 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0771 -4.2793 -4.7041 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9194 1.7284 -0.0844 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9474 2.6683 1.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0890 1.9472 3.5667 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7074 -0.6082 2.3405 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4924 1.6835 0.4732 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6974 -0.4825 -1.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8821 -0.0799 0.3045 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6096 -1.2735 0.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9365 1.9193 2.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7632 0.4668 4.2788 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4763 3.2192 1.3925 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1610 2.8288 3.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6005 1.0486 1.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7944 -1.4046 0.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0338 0.0762 2.8776 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6664 -0.0394 -0.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5391 2.1918 1.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6803 3.6169 -0.3255 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6426 2.3974 -1.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3300 3.4507 1.3251 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9696 0.8837 2.2192 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2430 -2.2968 2.2581 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1629 -2.4917 2.2821 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5884 -0.0814 -5.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6931 0.4938 -4.2098 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0894 1.3097 -4.4484 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 17 20 1 0 13 21 1 0 21 22 1 0 12 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 1 0 28 30 1 0 27 31 1 0 26 32 1 0 25 33 1 0 8 34 1 0 6 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 38 45 1 0 37 46 1 0 2 47 1 0 22 5 1 0 30 24 1 0 43 36 1 0 22 9 2 0 19 14 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 7 54 1 0 15 55 1 0 16 56 1 0 18 57 1 0 19 58 1 0 20 59 1 0 24 60 1 6 25 61 1 6 26 62 1 1 27 63 1 6 28 64 1 1 29 65 1 0 29 66 1 0 29 67 1 0 31 68 1 0 32 69 1 0 33 70 1 0 34 71 1 0 36 72 1 1 37 73 1 6 38 74 1 1 39 75 1 6 40 76 1 1 41 77 1 0 41 78 1 0 42 79 1 0 44 80 1 0 45 81 1 0 46 82 1 0 47 83 1 0 47 84 1 0 47 85 1 0 M END

Standard InCHIKey	OGYXOOJUJQIDOX-XKRLVHJLSA-N
Standard InCHI	InChI=1S/C32H38O15/c1-12(2)4-9-16-18(44-32-27(42)25(40)22(37)19(11-33)45-32)10-17(35)20-23(38)30(47-31-26(41)24(39)21(36)13(3)43-31)28(46-29(16)20)14-5-7-15(34)8-6-14/h4-8,10,13,19,21-22,24-27,31-37,39-42H,9,11H2,1-3H3/t13-,19+,21-,22+,24+,25-,26+,27+,31+,32+/m0/s1
SMILES	CC(=CCc1c(cc(c2c(=O)c(c(c3ccc(cc3)O)oc12)O[C@@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	662.22	Volume:	627.371 ? Van der Waals volume.
Dense:	1.056	LogP:	1.524 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.033 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.584 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	31.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.141	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.955	Fsp³:	0.469
MCE-18:	123.319 ? 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:	0.684	Fluc inhibitor:	0.267 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.83 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.912 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.085	Promiscuous compounds:	0.153

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.372	MDCK Permeability:	-5.139
Pgp-inhibitor:	0.0	Pgp-substrate:	0.761
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):	0.026
20% Bioavailability (F20%):	0.041	30% Bioavailability (F30%):	0.947
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.008
Plasma Protein Binding (PPB):	78.914%	Volume Distribution (VD):	-0.033
Fu:	22.029% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.162
BSEP inhibitor:	0.434

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.912
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

1.625

Half-life (T1/2):

5.433

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.14
Human Hepatotoxicity (H-HT):	0.601	Drug-induced Liver Injury (DILI):	0.913
AMES Toxicity:	0.868	Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.023	Skin Sensitization:	0.999
Carcinogencity:	0.027	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.991
Hematotoxicity:	0.129	Drug-induced Nephrotoxicity:	0.792
Genotoxicity:	0.827	RPMI-8226 Immunitoxicity:	0.078
A549 Cytotoxicity:	0.308	Hek293 Cytotoxicity:	0.406
BCF:	0.903 ? 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:	3.613 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.363 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.487 ? 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
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[19301817]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[21535810]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[22178178]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[22280831]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	Kunming, China	n.a.	PMID[24621197]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37872831]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Calyx	n.a.	n.a.	Database[FooDB]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	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 NPC32572 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	15146
0.1-0.2	30244
0.2-0.3	3334
0.3-0.4	793
0.4-0.5	241
0.5-0.6	76
0.6-0.7	16
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8605	High Similarity	NPC5319
0.7241	Intermediate Similarity	NPC66087
0.6932	Remote Similarity	NPC116458
0.6932	Remote Similarity	NPC246943
0.6421	Remote Similarity	NPC131745
0.6364	Remote Similarity	NPC297987
0.625	Remote Similarity	NPC249281
0.6196	Remote Similarity	NPC605784
0.617	Remote Similarity	NPC278419
0.617	Remote Similarity	NPC179198
0.6146	Remote Similarity	NPC183672
0.6111	Remote Similarity	NPC46420
0.6067	Remote Similarity	NPC77672
0.6067	Remote Similarity	NPC133671
0.6067	Remote Similarity	NPC135391
0.6067	Remote Similarity	NPC78263
0.6067	Remote Similarity	NPC250069
0.6	Remote Similarity	NPC8573
0.5955	Remote Similarity	NPC111929
0.5955	Remote Similarity	NPC320283
0.5955	Remote Similarity	NPC41121
0.5938	Remote Similarity	NPC480466
0.59	Remote Similarity	NPC35119
0.5789	Remote Similarity	NPC276377
0.5761	Remote Similarity	NPC24043
0.5761	Remote Similarity	NPC488080
0.5761	Remote Similarity	NPC169977
0.5743	Remote Similarity	NPC32641
0.5743	Remote Similarity	NPC256188
0.567	Remote Similarity	NPC251417
0.5657	Remote Similarity	NPC150164
0.5652	Remote Similarity	NPC136042
0.5638	Remote Similarity	NPC168584
0.5545	Remote Similarity	NPC64425
0.5543	Remote Similarity	NPC289667
0.5532	Remote Similarity	NPC59534
0.551	Remote Similarity	NPC480463
0.5484	Remote Similarity	NPC145038
0.5484	Remote Similarity	NPC56077
0.5484	Remote Similarity	NPC281131
0.5484	Remote Similarity	NPC253662
0.5484	Remote Similarity	NPC179950
0.5484	Remote Similarity	NPC88789
0.5484	Remote Similarity	NPC491374
0.5446	Remote Similarity	NPC186816
0.5426	Remote Similarity	NPC271692
0.5413	Remote Similarity	NPC25523
0.5405	Remote Similarity	NPC483158
0.5405	Remote Similarity	NPC483157
0.5385	Remote Similarity	NPC288084
0.5376	Remote Similarity	NPC127546
0.5376	Remote Similarity	NPC57625
0.5376	Remote Similarity	NPC173637
0.5376	Remote Similarity	NPC317489
0.5376	Remote Similarity	NPC223424
0.5376	Remote Similarity	NPC600591
0.5319	Remote Similarity	NPC64305
0.53	Remote Similarity	NPC139320
0.5288	Remote Similarity	NPC72016
0.5273	Remote Similarity	NPC164704
0.5263	Remote Similarity	NPC84362
0.5243	Remote Similarity	NPC240306
0.5213	Remote Similarity	NPC39360
0.5213	Remote Similarity	NPC29763
0.5213	Remote Similarity	NPC210003
0.5208	Remote Similarity	NPC472459
0.5208	Remote Similarity	NPC599850
0.5158	Remote Similarity	NPC323593
0.5158	Remote Similarity	NPC203500
0.5155	Remote Similarity	NPC488071
0.5152	Remote Similarity	NPC203050
0.5152	Remote Similarity	NPC225434
0.5106	Remote Similarity	NPC331652
0.5104	Remote Similarity	NPC349108
0.51	Remote Similarity	NPC265115
0.5098	Remote Similarity	NPC173582
0.5098	Remote Similarity	NPC265885
0.5098	Remote Similarity	NPC181465
0.5098	Remote Similarity	NPC215710
0.5098	Remote Similarity	NPC163242
0.5098	Remote Similarity	NPC272068
0.5098	Remote Similarity	NPC473438
0.5098	Remote Similarity	NPC253788
0.5053	Remote Similarity	NPC19388
0.5053	Remote Similarity	NPC240431
0.5053	Remote Similarity	NPC55786
0.5053	Remote Similarity	NPC476405
0.5053	Remote Similarity	NPC108831
0.5053	Remote Similarity	NPC182634
0.5052	Remote Similarity	NPC42773
0.5052	Remote Similarity	NPC45522
0.5051	Remote Similarity	NPC223747
0.5046	Remote Similarity	NPC14187
0.5044	Remote Similarity	NPC470716

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC32572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4210
0.1-0.2	4871
0.2-0.3	55
0.3-0.4	10
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD7804	Clinical (unspecified phase)

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