NPASS Compound

Natural Product: NPC573244

Natural Product ID	NPC573244
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-[[(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},9~{S},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{R})-3~{a}-carboxy-1-isopropenyl-5~{a},5~{b},8,8,11~{a}-pentamethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	6-[[(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},9~{S},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{R})-3~{a}-carboxy-1-isopropenyl-5~{a},5~{b},8,8,11~{a}-pentamethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 101106 0 0 0 0 0 0 0 0999 V2000 -7.2982 -0.0455 -3.1349 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0910 -0.2935 -2.7121 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9780 0.3466 -3.5046 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7505 -1.1567 -1.5310 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0206 -1.6177 -0.8787 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1757 -0.7007 0.3485 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7412 -0.6760 0.8023 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3524 -1.9604 1.3623 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2011 -2.0349 2.6333 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1132 -3.1491 0.7001 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3835 0.4787 1.6734 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8955 0.4826 1.8988 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0706 0.5134 0.6307 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1576 1.9173 0.1222 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6122 -0.5578 -0.2670 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7339 -0.8975 -1.4244 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3864 -1.3333 -0.7991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -0.0368 -0.2343 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6528 -0.0277 -0.1222 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2088 -1.3437 0.2908 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1883 0.2293 -1.5486 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6553 0.3226 -1.6305 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3834 0.8263 -0.4126 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2607 -0.1570 0.0861 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6009 0.1242 -0.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0206 -0.8205 -1.1162 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3626 -0.8674 -1.3335 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9418 0.3097 -2.0133 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1832 1.2440 -2.3617 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3022 0.4177 -2.2809 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1016 -1.2475 -0.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0910 -0.3111 0.2414 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1038 -1.3088 1.0874 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7673 -1.4991 2.2778 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4072 0.0625 1.0767 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4459 1.0180 0.9760 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5681 1.4219 0.6526 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7934 2.9538 0.6498 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1148 0.9637 1.9868 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0902 1.1631 0.6325 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4199 1.2509 1.9636 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0699 1.5262 1.6840 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6159 0.2635 1.0085 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5593 -0.7984 2.0454 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0415 -0.3426 -0.5327 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4115 0.6077 -4.0329 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2393 -0.3685 -2.7535 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 -0.3865 -3.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4046 0.9320 -4.3376 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4906 1.0901 -2.8416 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1496 -2.0198 -1.9212 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9389 -1.5428 -1.4328 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8634 -2.6799 -0.5599 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5229 0.2720 0.0048 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8474 -1.2317 1.0382 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3361 -4.0615 1.1232 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8565 0.3318 2.6659 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7410 1.4036 1.1761 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6013 1.3427 2.5721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6533 -0.4797 2.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1073 2.2374 -0.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3720 2.2429 -0.5558 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0434 2.5746 1.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5527 -1.4911 0.3793 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1219 -1.8130 -1.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5413 -0.0554 -2.1231 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7629 -1.7796 -1.5708 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6433 -2.0816 -0.0531 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0845 0.7497 -0.9809 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6663 -1.4001 1.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9951 -1.7429 -0.4204 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3828 -2.1071 0.1585 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7335 1.2112 -1.8462 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 -0.5621 -2.2364 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1305 -0.6678 -1.8997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8809 0.9517 -2.5427 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0897 1.6079 -0.8303 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6377 1.1143 -0.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5174 -1.7250 -2.0725 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6957 1.3378 -2.3889 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5249 -2.2673 -0.1500 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9774 -0.6895 0.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3756 -2.0858 0.8363 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6301 -2.4352 2.5637 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8887 0.2394 2.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0926 1.9153 1.1479 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8339 3.1904 0.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1512 3.3619 -0.1738 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4462 3.4071 1.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5282 -0.0633 1.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9934 1.6309 2.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4169 1.1145 2.8134 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6575 2.0373 0.0411 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7720 2.1829 2.4765 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5527 0.4149 2.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0282 2.3851 0.9650 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5995 1.7342 2.6087 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7710 -0.3411 3.0318 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1873 -1.6905 1.8706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5284 -1.2208 2.1915 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3363 0.7158 -0.7113 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 8 9 2 0 8 10 1 0 7 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 23 37 1 0 37 38 1 0 37 39 1 0 37 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 1 15 45 1 0 45 4 1 0 45 7 1 0 43 13 1 0 43 18 1 0 40 19 1 0 35 25 1 0 1 46 1 0 1 47 1 0 3 48 1 0 3 49 1 0 3 50 1 0 4 51 1 6 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 10 56 1 0 11 57 1 0 11 58 1 0 12 59 1 0 12 60 1 0 14 61 1 0 14 62 1 0 14 63 1 0 15 64 1 1 16 65 1 0 16 66 1 0 17 67 1 0 17 68 1 0 18 69 1 6 20 70 1 0 20 71 1 0 20 72 1 0 21 73 1 0 21 74 1 0 22 75 1 0 22 76 1 0 23 77 1 6 25 78 1 0 27 79 1 0 30 80 1 0 31 81 1 0 32 82 1 0 33 83 1 0 34 84 1 0 35 85 1 0 36 86 1 0 38 87 1 0 38 88 1 0 38 89 1 0 39 90 1 0 39 91 1 0 39 92 1 0 40 93 1 6 41 94 1 0 41 95 1 0 42 96 1 0 42 97 1 0 44 98 1 0 44 99 1 0 44100 1 0 45101 1 6 M END

Standard InCHIKey	SQYXYJWZICEBBS-ULMIPHOXSA-N
Standard InCHI	InChI=1S/C36H56O9/c1-18(2)19-10-15-36(31(42)43)17-16-34(6)20(24(19)36)8-9-22-33(5)13-12-23(32(3,4)21(33)11-14-35(22,34)7)44-30-27(39)25(37)26(38)28(45-30)29(40)41/h19-28,30,37-39H,1,8-17H2,2-7H3,(H,40,41)(H,42,43)/t19-,20+,21-,22+,23-,24+,25?,26?,27?,28?,30?,33-,34+,35+,36-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	632.39	Volume:	651.076 ? Van der Waals volume.
Dense:	0.971	LogP:	3.151 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.879 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.183 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	34.0
TPSA:	153.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.208	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.284	Fsp³:	0.889
MCE-18:	129.941 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.709	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.099	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.845	MDCK Permeability:	-5.182
Pgp-inhibitor:	0.0	Pgp-substrate:	0.029
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):	0.008
20% Bioavailability (F20%):	0.151	30% Bioavailability (F30%):	0.247
50% Bioavailability (F50%):	0.771

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	83.177%	Volume Distribution (VD):	-0.588
Fu:	13.071% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.686
OATP1B3 inhibitor:	0.157	BCRP inhibitor:	0.0
BSEP inhibitor:	0.006

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.834	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.987	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

0.399

Half-life (T1/2):

1.997

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.718	Drug-induced Liver Injury (DILI):	0.908
AMES Toxicity:	0.135	Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.381	Skin Sensitization:	0.652
Carcinogencity:	0.692	Eye Corrosion:	0.001
Eye Irritation:	0.269	Respiratory Toxicity:	0.635
Drug-induced Neurotoxicity:	0.028	Ototoxicity:	0.904
Hematotoxicity:	0.277	Drug-induced Nephrotoxicity:	0.833
Genotoxicity:	0.611	RPMI-8226 Immunitoxicity:	0.012
A549 Cytotoxicity:	0.006	Hek293 Cytotoxicity:	0.056
BCF:	0.477 ? 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:	3.487 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.159 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.326 ? 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
NPO5283	Schefflera actinophylla	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5283	Schefflera actinophylla	Species	Araliaceae	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 NPC573244 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	21084
0.1-0.2	24456
0.2-0.3	3678
0.3-0.4	475
0.4-0.5	120
0.5-0.6	30
0.6-0.7	10
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	Natural Product ID
0.6447	Remote Similarity	NPC4309
0.6395	Remote Similarity	NPC88744
0.6316	Remote Similarity	NPC271974
0.6316	Remote Similarity	NPC247312
0.6282	Remote Similarity	NPC160506
0.6087	Remote Similarity	NPC51947
0.6067	Remote Similarity	NPC286347
0.6053	Remote Similarity	NPC264317
0.6053	Remote Similarity	NPC294438
0.602	Remote Similarity	NPC204392
0.5842	Remote Similarity	NPC275668
0.5769	Remote Similarity	NPC488164
0.5769	Remote Similarity	NPC264005
0.5625	Remote Similarity	NPC16377
0.561	Remote Similarity	NPC478841
0.561	Remote Similarity	NPC488166
0.551	Remote Similarity	NPC488205
0.55	Remote Similarity	NPC201655
0.5446	Remote Similarity	NPC240734
0.5417	Remote Similarity	NPC480938
0.5375	Remote Similarity	NPC488506
0.5375	Remote Similarity	NPC220498
0.5375	Remote Similarity	NPC213832
0.5325	Remote Similarity	NPC68828
0.5312	Remote Similarity	NPC482752
0.5288	Remote Similarity	NPC91838
0.5263	Remote Similarity	NPC248287
0.5263	Remote Similarity	NPC234548
0.525	Remote Similarity	NPC80590
0.5244	Remote Similarity	NPC151191
0.5208	Remote Similarity	NPC294112
0.5208	Remote Similarity	NPC480937
0.5204	Remote Similarity	NPC488208
0.5158	Remote Similarity	NPC224414
0.5155	Remote Similarity	NPC8102
0.5155	Remote Similarity	NPC66894
0.5125	Remote Similarity	NPC192744
0.5119	Remote Similarity	NPC488165
0.505	Remote Similarity	NPC309780
0.5047	Remote Similarity	NPC488206

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC573244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6045
0.1-0.2	3014
0.2-0.3	86
0.3-0.4	0
0.4-0.5	2
0.5-0.6	0
0.6-0.7	3
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
0.6282	Remote Similarity	NPD8035	Phase 2
0.6053	Remote Similarity	NPD7520	Phase 1
0.6044	Remote Similarity	NPD8034	Phase 2

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