NPASS Compound

Natural Product: NPC329784

Natural Product ID	NPC329784
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Boivinide E
IUPAC Name	(3S,5S,8R,9S,10R,13R,14S,17R)-14-hydroxy-3-[(2R,4S,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carboxylic acid
Synonyms	boivinide E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL249845
PubChem CID	44445752
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 104110 0 0 0 0 0 0 0 0999 V2000 5.1377 1.6112 2.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 1.8918 1.1715 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4586 0.8788 0.5454 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2235 1.3739 -0.1979 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4370 0.1231 -0.5771 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2978 0.0281 0.2201 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1865 0.0987 -0.6113 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6489 -1.1616 -0.5439 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6248 -1.1713 0.5817 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5813 0.0234 0.5701 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0987 0.9133 -0.5367 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6766 1.3062 -0.2908 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9993 2.0844 -0.8288 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3052 1.4550 -1.3364 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8678 0.6781 -0.1769 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9773 -0.4627 0.1467 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5615 -1.4186 1.1144 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8593 -1.1003 1.7258 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8373 -0.2822 0.9381 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2787 0.2465 -0.3736 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0916 1.2948 -0.7640 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4743 -0.8866 -1.3527 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3161 -1.9174 -0.6231 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9584 -1.1631 0.5071 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2108 -0.5644 0.1075 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7337 -0.6841 -1.0939 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9991 0.0265 -1.1923 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7464 0.1097 -2.1974 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2297 0.5909 0.0143 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1686 0.2771 0.8837 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2276 0.8931 1.8075 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5538 0.6316 1.8917 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8233 0.1241 2.7997 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2619 1.7529 2.3015 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1801 -1.0226 -0.4233 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4256 -0.9957 -1.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2886 0.1194 -0.4654 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4805 -0.2976 0.0732 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5539 0.2791 -0.6152 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2695 -0.7110 -1.2355 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3118 -1.2439 -0.5207 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8891 -2.0017 0.7167 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0635 -3.0576 0.3578 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3708 -0.2323 -0.2097 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8441 1.1564 -0.0606 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3694 1.1959 0.2598 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9731 2.5422 0.0830 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5256 1.7717 0.9882 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3100 -0.2228 -1.2476 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0788 -2.3483 -0.7083 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0828 1.5684 2.9157 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7471 2.3552 3.0754 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5759 0.5980 2.7454 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0761 0.1069 1.2675 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6653 2.0100 0.5106 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5494 1.9452 -1.0817 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1941 0.2293 -1.6531 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4876 0.2113 -1.6740 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0736 -1.4556 -1.5257 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0902 -1.9843 -0.3085 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1687 -2.1240 0.5605 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0241 -1.1892 1.5363 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1180 0.2884 -1.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4437 2.1607 -0.9706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4678 1.5780 0.7638 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1618 2.7529 0.0090 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5699 2.6362 -1.6677 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9335 2.2808 -1.6722 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0278 0.8252 -2.1951 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8700 1.3853 0.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7543 -0.9752 -0.8407 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5141 -2.4535 0.6575 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8040 -1.5237 1.9535 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3337 -2.0928 2.0057 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6725 -0.6523 2.7509 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6895 2.1813 -0.6250 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0044 -0.5287 -2.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5620 -1.3757 -1.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6884 -2.7657 -0.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0040 -2.3759 -1.3380 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1210 -1.9259 1.3272 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3592 -1.2171 -1.9914 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7771 1.2385 1.2067 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6240 -0.3150 1.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4712 1.8026 1.2257 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3269 1.2304 2.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9529 0.6197 2.5868 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3877 2.0043 3.2791 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3277 -0.9538 -2.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4663 0.8229 -1.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1380 0.9354 -1.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7770 -2.0232 -1.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8305 -2.4204 1.1583 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3913 -1.3899 1.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6918 -3.5221 1.1339 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9379 -0.5722 0.6979 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0356 1.7693 -0.9746 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2411 1.0002 1.3422 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5581 2.6461 -0.8129 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8556 2.6716 0.7537 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8131 -0.4989 -2.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3250 -3.1457 -0.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3836 -2.3930 0.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9561 -2.5120 -1.3424 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 1 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 19 31 1 1 10 32 1 1 32 33 2 0 32 34 1 0 5 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 42 43 1 0 41 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 45 48 1 0 44 49 1 0 36 50 1 0 37 3 1 0 46 39 1 0 12 7 1 0 20 15 1 0 30 25 1 0 16 10 1 0 24 19 1 0 1 51 1 0 1 52 1 0 1 53 1 0 3 54 1 1 4 55 1 0 4 56 1 0 5 57 1 6 7 58 1 6 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 11 63 1 6 12 64 1 0 12 65 1 0 13 66 1 0 13 67 1 0 14 68 1 0 14 69 1 0 15 70 1 1 16 71 1 6 17 72 1 0 17 73 1 0 18 74 1 0 18 75 1 0 21 76 1 0 22 77 1 0 22 78 1 0 23 79 1 0 23 80 1 0 24 81 1 1 26 82 1 0 30 83 1 0 30 84 1 0 31 85 1 0 31 86 1 0 31 87 1 0 34 88 1 0 36 89 1 6 37 90 1 6 39 91 1 6 41 92 1 6 42 93 1 0 42 94 1 0 43 95 1 0 44 96 1 1 45 97 1 6 46 98 1 1 47 99 1 0 48100 1 0 49101 1 0 50102 1 0 50103 1 0 50104 1 0 M END

Standard InCHIKey	YRNGTFHYGBEEKX-RDLUFXFASA-N
Standard InCHI	InChI=1S/C36H54O14/c1-17-31(50-32-30(41)29(40)28(39)25(15-37)49-32)24(45-3)14-27(47-17)48-20-6-10-35(33(42)43)19(13-20)4-5-23-22(35)7-9-34(2)21(8-11-36(23,34)44)18-12-26(38)46-16-18/h12,17,19-25,27-32,37,39-41,44H,4-11,13-16H2,1-3H3,(H,42,43)/t17-,19+,20+,21-,22+,23-,24+,25-,27+,28-,29+,30-,31+,32+,34-,35-,36+/m1/s1
SMILES	CO[C@H]1C[C@H](O[C@H]2CC[C@]3([C@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C(=O)O)O[C@@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	710.35	Volume:	686.471 ? Van der Waals volume.
Dense:	1.035	LogP:	-0.177 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.951 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.086 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	39.0
TPSA:	210.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.154	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.707	Fsp³:	0.889
MCE-18:	132.706 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.751	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.153	Promiscuous compounds:	0.204

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.878	MDCK Permeability:	-5.336
Pgp-inhibitor:	0.0	Pgp-substrate:	0.922
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):	0.237
20% Bioavailability (F20%):	0.264	30% Bioavailability (F30%):	0.402
50% Bioavailability (F50%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.853
Plasma Protein Binding (PPB):	60.48%	Volume Distribution (VD):	-0.524
Fu:	37.68% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.005
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.232	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.058	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.009 ? 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):

1.317

Half-life (T1/2):

3.609

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.05
Human Hepatotoxicity (H-HT):	0.72	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.998	Skin Sensitization:	1.0
Carcinogencity:	0.76	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.889
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.98
Hematotoxicity:	0.878	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.777
A549 Cytotoxicity:	0.782	Hek293 Cytotoxicity:	0.942
BCF:	0.501 ? 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:	3.224 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.76 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.804 ? 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
NPO33407	roupellina boivinii	Species	n.a.	n.a.	n.a.	Madagascar rainforest	n.a.	PMID[17988099]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell line	A2780	Homo sapiens	IC50	=	280.0	nM	PMID[23822611]

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 NPC329784 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	13250
0.1-0.2	31424
0.2-0.3	4657
0.3-0.4	362
0.4-0.5	95
0.5-0.6	53
0.6-0.7	10
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8646	High Similarity	NPC486140
0.8137	Intermediate Similarity	NPC486152
0.7579	Intermediate Similarity	NPC27363
0.697	Remote Similarity	NPC486151
0.6863	Remote Similarity	NPC329986
0.6863	Remote Similarity	NPC140092
0.6538	Remote Similarity	NPC146857
0.6481	Remote Similarity	NPC475419
0.6273	Remote Similarity	NPC329675
0.625	Remote Similarity	NPC474423
0.6126	Remote Similarity	NPC194716
0.6036	Remote Similarity	NPC74259
0.6	Remote Similarity	NPC486130
0.5982	Remote Similarity	NPC474908
0.5943	Remote Similarity	NPC486127
0.5893	Remote Similarity	NPC120390
0.5888	Remote Similarity	NPC486143
0.5888	Remote Similarity	NPC486135
0.5888	Remote Similarity	NPC486142
0.5888	Remote Similarity	NPC486137
0.5888	Remote Similarity	NPC486149
0.5833	Remote Similarity	NPC232785
0.5833	Remote Similarity	NPC486139
0.5794	Remote Similarity	NPC475629
0.5676	Remote Similarity	NPC486132
0.5676	Remote Similarity	NPC486131
0.5636	Remote Similarity	NPC486146
0.5625	Remote Similarity	NPC486128
0.5596	Remote Similarity	NPC125077
0.5588	Remote Similarity	NPC5311
0.5588	Remote Similarity	NPC77299
0.5588	Remote Similarity	NPC480906
0.5586	Remote Similarity	NPC486138
0.5586	Remote Similarity	NPC276838
0.5575	Remote Similarity	NPC486144
0.5575	Remote Similarity	NPC486145
0.5575	Remote Similarity	NPC486147
0.5575	Remote Similarity	NPC486136
0.5575	Remote Similarity	NPC486148
0.5556	Remote Similarity	NPC475556
0.5556	Remote Similarity	NPC311706
0.5534	Remote Similarity	NPC480914
0.549	Remote Similarity	NPC84987
0.5413	Remote Similarity	NPC480910
0.5413	Remote Similarity	NPC480909
0.5385	Remote Similarity	NPC486133
0.5327	Remote Similarity	NPC480907
0.5321	Remote Similarity	NPC236973
0.5321	Remote Similarity	NPC32177
0.5321	Remote Similarity	NPC469756
0.5321	Remote Similarity	NPC275901
0.5304	Remote Similarity	NPC475590
0.5299	Remote Similarity	NPC117445
0.5299	Remote Similarity	NPC308262
0.5299	Remote Similarity	NPC486134
0.5299	Remote Similarity	NPC486141
0.5273	Remote Similarity	NPC188234
0.5273	Remote Similarity	NPC240070
0.5254	Remote Similarity	NPC486150
0.5229	Remote Similarity	NPC30483
0.5229	Remote Similarity	NPC470897
0.5221	Remote Similarity	NPC247190
0.5182	Remote Similarity	NPC292467
0.5094	Remote Similarity	NPC76572
0.5094	Remote Similarity	NPC193382
0.5043	Remote Similarity	NPC329636

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC329784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4859
0.1-0.2	4156
0.2-0.3	117
0.3-0.4	9
0.4-0.5	9
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data