NPASS Compound

Natural Product: NPC177246

Natural Product ID	NPC177246
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-(Alpha-L-Arabinopyranosyl)-23-Hydroxyursolic Acid
IUPAC Name	(1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL506997
PubChem CID	21589722
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 99104 0 0 0 0 0 0 0 0999 V2000 -4.7865 1.8300 -3.6066 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1164 0.8583 -2.5364 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8130 1.4691 -1.3418 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3320 0.3195 -0.5494 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3050 -0.6952 -0.1197 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9711 -0.3720 1.3140 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7098 -0.9503 1.8537 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5036 -0.6271 0.9502 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4692 0.8755 0.9259 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8924 -1.2511 -0.3193 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1273 -2.1727 -0.8416 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8577 -2.6719 -0.2595 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2695 -1.4968 0.4833 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1765 -1.6964 0.8298 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5091 -2.9962 1.4799 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9263 -1.6716 -0.4909 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4191 -1.5298 -0.2949 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6492 -0.1932 0.3534 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0837 -0.2794 1.7466 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7995 -1.2100 2.6476 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2730 1.1294 2.3357 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5886 2.0450 1.5717 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6226 -0.4869 1.6087 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8162 -0.4382 2.8673 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5868 -0.0175 2.4045 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2112 -1.1104 1.5484 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5590 -2.2160 2.5161 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8897 0.3162 0.2205 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0430 1.4460 -0.5280 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8253 2.5586 0.1056 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8104 3.0922 -0.9313 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1014 3.2850 -2.2673 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5690 1.9552 -2.7057 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7801 1.0424 -1.6744 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0118 3.7579 -3.1799 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 2.1339 -1.1209 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0194 3.6190 0.5163 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1427 -0.8813 -1.0212 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8571 0.2090 -1.9972 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1429 -0.3159 -3.2633 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0710 -1.9879 -0.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2879 -2.0834 -0.3065 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4083 -3.1604 0.3094 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8733 2.4247 -3.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6410 2.5678 -3.6562 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8069 1.3106 -4.5867 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7316 0.0404 -2.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0668 2.0980 -0.8326 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7038 2.0668 -1.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1488 -0.1513 -1.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8699 0.7524 0.3268 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7796 -0.8071 1.9919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0650 0.7081 1.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8760 -2.0434 1.9393 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5684 -0.4712 2.8529 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3028 1.1833 2.0026 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6757 1.3227 0.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4022 1.3704 0.6630 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4180 -2.6508 -1.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0795 -3.5478 0.4063 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1786 -3.0756 -1.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2759 -0.6502 -0.2706 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7146 -2.9304 2.5684 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7134 -3.7304 1.2469 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4460 -3.4763 1.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8071 -2.6566 -1.0301 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5607 -0.8876 -1.1690 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8995 -2.3735 0.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8483 -1.4591 -1.3332 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9480 0.4959 -0.2128 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 -2.1447 2.1996 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1945 -1.3373 3.5709 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7311 -0.6807 3.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0210 1.1235 3.4091 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3848 1.3347 2.2866 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6458 2.9213 2.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2718 0.3909 0.9796 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1552 0.3987 3.5047 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7999 -1.3481 3.4582 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1426 0.1952 3.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3440 0.8876 1.7901 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6600 -2.6998 2.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0722 -1.7395 3.3788 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1331 -3.0482 2.0623 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1156 1.8686 -0.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4227 2.2581 0.9845 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2848 4.0241 -0.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3001 4.0465 -2.1761 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4769 1.9714 -2.9026 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0876 1.5684 -3.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1399 3.0977 -3.9152 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9127 1.9130 -2.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8572 4.2775 -0.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4277 -1.7413 -1.7153 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1921 1.0120 -1.6554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0253 0.5495 -3.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7128 -1.1492 -3.6841 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1086 -0.6414 -3.0381 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9086 -4.0514 0.3924 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 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 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 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 18 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 10 38 1 0 38 39 1 0 39 40 1 0 5 41 1 1 41 42 2 0 41 43 1 0 39 2 1 0 38 5 1 0 26 8 1 0 34 29 1 0 26 13 1 0 23 14 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 6 52 1 0 6 53 1 0 7 54 1 0 7 55 1 0 9 56 1 0 9 57 1 0 9 58 1 0 11 59 1 0 12 60 1 0 12 61 1 0 13 62 1 6 15 63 1 0 15 64 1 0 15 65 1 0 16 66 1 0 16 67 1 0 17 68 1 0 17 69 1 0 18 70 1 6 20 71 1 0 20 72 1 0 20 73 1 0 21 74 1 0 21 75 1 0 22 76 1 0 23 77 1 6 24 78 1 0 24 79 1 0 25 80 1 0 25 81 1 0 27 82 1 0 27 83 1 0 27 84 1 0 29 85 1 6 30 86 1 1 31 87 1 1 32 88 1 1 33 89 1 0 33 90 1 0 35 91 1 0 36 92 1 0 37 93 1 0 38 94 1 6 39 95 1 1 40 96 1 0 40 97 1 0 40 98 1 0 43 99 1 0 M END

Standard InCHIKey	VLKSXELFNUEYKM-OHOLNXJGSA-N
Standard InCHI	InChI=1S/C35H56O8/c1-19-9-14-35(30(40)41)16-15-33(5)21(26(35)20(19)2)7-8-24-31(3)12-11-25(43-29-28(39)27(38)22(37)17-42-29)32(4,18-36)23(31)10-13-34(24,33)6/h7,19-20,22-29,36-39H,8-18H2,1-6H3,(H,40,41)/t19-,20+,22+,23-,24-,25+,26+,27+,28-,29+,31+,32+,33-,34-,35+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	604.4	Volume:	627.626 ? Van der Waals volume.
Dense:	0.963	LogP:	3.177 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.052 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.892 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	136.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.233	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.359	Fsp³:	0.914
MCE-18:	123.582 ? 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:	0.918	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.038 ? 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:	0.158	Promiscuous compounds:	0.073

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.803	MDCK Permeability:	-5.198
Pgp-inhibitor:	0.001	Pgp-substrate:	0.037
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):	0.005
20% Bioavailability (F20%):	0.39	30% Bioavailability (F30%):	0.125
50% Bioavailability (F50%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.407	MRP1:	0.856
Plasma Protein Binding (PPB):	79.979%	Volume Distribution (VD):	-0.599
Fu:	14.376% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.178	BCRP inhibitor:	0.161
BSEP inhibitor:	0.557

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	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:	0.462	CYP3A4-substrate:	0.108
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):

0.786

Half-life (T1/2):

1.523

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.759	Drug-induced Liver Injury (DILI):	0.85
AMES Toxicity:	0.663	Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.049	Skin Sensitization:	0.998
Carcinogencity:	0.809	Eye Corrosion:	0.001
Eye Irritation:	0.287	Respiratory Toxicity:	0.654
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.857
Hematotoxicity:	0.811	Drug-induced Nephrotoxicity:	0.962
Genotoxicity:	0.613	RPMI-8226 Immunitoxicity:	0.047
A549 Cytotoxicity:	0.486	Hek293 Cytotoxicity:	0.223
BCF:	0.919 ? 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:	3.545 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.096 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.342 ? 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
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510614]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24490	Cussonia bancoensis	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

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell line	2

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	47900.0	nM	PMID[18760602]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	124000.0	nM	PMID[24268596]

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 NPC177246 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	18920
0.1-0.2	25292
0.2-0.3	4219
0.3-0.4	959
0.4-0.5	365
0.5-0.6	70
0.6-0.7	24
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8101	Intermediate Similarity	NPC57362
0.7875	Intermediate Similarity	NPC28198
0.7875	Intermediate Similarity	NPC476123
0.7024	Intermediate Similarity	NPC283849
0.6782	Remote Similarity	NPC100383
0.641	Remote Similarity	NPC51700
0.641	Remote Similarity	NPC88716
0.641	Remote Similarity	NPC68160
0.6375	Remote Similarity	NPC485589
0.6329	Remote Similarity	NPC61543
0.6329	Remote Similarity	NPC293048
0.6329	Remote Similarity	NPC225585
0.6322	Remote Similarity	NPC204407
0.6237	Remote Similarity	NPC127853
0.619	Remote Similarity	NPC230151
0.6129	Remote Similarity	NPC473481
0.6105	Remote Similarity	NPC136877
0.6087	Remote Similarity	NPC284807
0.6082	Remote Similarity	NPC6377
0.6082	Remote Similarity	NPC488561
0.6082	Remote Similarity	NPC208381
0.6071	Remote Similarity	NPC485586
0.6071	Remote Similarity	NPC485588
0.6049	Remote Similarity	NPC173089
0.6044	Remote Similarity	NPC242611
0.6042	Remote Similarity	NPC174679
0.6042	Remote Similarity	NPC279554
0.6042	Remote Similarity	NPC59804
0.5876	Remote Similarity	NPC108748
0.5854	Remote Similarity	NPC32407
0.5854	Remote Similarity	NPC263548
0.5854	Remote Similarity	NPC606320
0.5842	Remote Similarity	NPC104400
0.5842	Remote Similarity	NPC10320
0.5806	Remote Similarity	NPC256798
0.58	Remote Similarity	NPC469945
0.575	Remote Similarity	NPC274050
0.575	Remote Similarity	NPC162632
0.5745	Remote Similarity	NPC473538
0.5732	Remote Similarity	NPC71074
0.5732	Remote Similarity	NPC605937
0.5729	Remote Similarity	NPC270667
0.5714	Remote Similarity	NPC606107
0.5679	Remote Similarity	NPC274330
0.5673	Remote Similarity	NPC79718
0.5663	Remote Similarity	NPC87095
0.5636	Remote Similarity	NPC323341
0.5577	Remote Similarity	NPC481082
0.5577	Remote Similarity	NPC164419
0.5556	Remote Similarity	NPC485585
0.5543	Remote Similarity	NPC485882
0.55	Remote Similarity	NPC127056
0.5481	Remote Similarity	NPC258885
0.5476	Remote Similarity	NPC477288
0.5472	Remote Similarity	NPC276093
0.5464	Remote Similarity	NPC189884
0.5464	Remote Similarity	NPC138334
0.5455	Remote Similarity	NPC12288
0.5429	Remote Similarity	NPC73829
0.5426	Remote Similarity	NPC286347
0.54	Remote Similarity	NPC56713
0.5368	Remote Similarity	NPC485587
0.5349	Remote Similarity	NPC127689
0.5347	Remote Similarity	NPC178093
0.5333	Remote Similarity	NPC139044
0.5333	Remote Similarity	NPC471383
0.5312	Remote Similarity	NPC173569
0.5301	Remote Similarity	NPC477289
0.5294	Remote Similarity	NPC305464
0.5294	Remote Similarity	NPC295371
0.5294	Remote Similarity	NPC19376
0.5294	Remote Similarity	NPC488516
0.5294	Remote Similarity	NPC25848
0.5278	Remote Similarity	NPC477191
0.5273	Remote Similarity	NPC280941
0.5273	Remote Similarity	NPC235772
0.5269	Remote Similarity	NPC274507
0.5263	Remote Similarity	NPC224121
0.5258	Remote Similarity	NPC294112
0.5254	Remote Similarity	NPC471385
0.5243	Remote Similarity	NPC479745
0.5243	Remote Similarity	NPC475171
0.5229	Remote Similarity	NPC488209
0.5229	Remote Similarity	NPC477192
0.5221	Remote Similarity	NPC471384
0.5217	Remote Similarity	NPC484195
0.5196	Remote Similarity	NPC482748
0.5175	Remote Similarity	NPC166422
0.5155	Remote Similarity	NPC128925
0.5152	Remote Similarity	NPC90856
0.51	Remote Similarity	NPC164194
0.5098	Remote Similarity	NPC304110
0.5098	Remote Similarity	NPC27518
0.5098	Remote Similarity	NPC611516
0.5093	Remote Similarity	NPC488515
0.5088	Remote Similarity	NPC133818
0.5051	Remote Similarity	NPC195132
0.505	Remote Similarity	NPC179434

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC177246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6079
0.1-0.2	3002
0.2-0.3	59
0.3-0.4	9
0.4-0.5	1
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