NPASS Compound

Natural Product: NPC172311

Natural Product ID	NPC172311
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-O-Cis-P-Coumaroyl-20Beta-Hydroxy-12-Ursen-28-Oic Acid
IUPAC Name	(1R,2S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2-hydroxy-10-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505587
PubChem CID	11692990
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 6.2087 0.2133 0.6970 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6174 0.2457 -0.3858 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2184 0.3338 -0.2714 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5669 0.3801 0.9764 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8673 1.6890 1.2226 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3815 1.6465 1.1269 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8991 0.6200 0.0924 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2972 -0.7157 0.6289 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7095 -0.8313 1.0968 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7885 -1.2875 2.5677 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4092 -1.9504 0.3378 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8800 -1.7569 -0.3524 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5990 -1.7730 -0.5534 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2816 -0.4398 -0.5871 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6193 0.6444 0.1564 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2203 1.9567 -0.1323 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6933 1.8463 -0.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4139 0.7316 -0.1156 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6933 -0.5805 0.0054 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5146 -0.8123 1.5100 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4267 -1.7309 -0.5572 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6603 -1.5036 -1.3234 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3387 -0.1998 -1.2357 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9280 0.7459 -0.1830 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6054 0.7398 1.1187 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8971 2.1846 1.5933 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7956 -0.0898 1.3527 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6783 -0.9764 2.5925 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8887 0.7616 1.6588 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2659 -0.9150 0.1937 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8632 -0.3873 -1.1293 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2209 0.5085 -2.5725 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6718 0.0194 -3.5656 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7840 1.7788 -2.6168 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4913 -0.0984 -2.0526 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4174 1.0139 -1.2125 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1304 0.2084 -1.7253 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3779 0.1882 -2.0672 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5171 0.2202 -1.1986 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6175 -0.5491 -1.6388 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8000 -0.5168 -0.9716 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9226 0.2776 0.1474 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8835 1.0397 0.6072 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6784 1.0037 -0.0801 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1427 0.2932 0.8154 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3683 0.3271 1.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1157 2.1261 2.2237 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3233 2.4201 0.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9404 1.4177 2.1024 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0347 2.6356 0.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6648 -0.8949 1.5296 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6888 -1.8734 2.7587 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8312 -0.3760 3.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8458 -1.8126 2.8498 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3843 -1.8385 -0.7411 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5066 -1.9400 0.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0631 -2.9421 0.7189 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4374 -1.7294 -1.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1395 -2.7597 0.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7264 -2.3008 -1.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0947 -2.4811 0.1565 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7879 0.4618 1.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 2.7334 0.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9334 2.4187 -1.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3080 2.7725 -0.2590 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3950 -1.4491 1.8333 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6224 -1.3765 1.7687 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5450 0.0858 2.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6422 -2.4890 0.2623 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7105 -2.3197 -1.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4164 -2.3016 -1.0418 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5031 -1.7506 -2.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1482 1.7788 -0.6242 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8542 0.4144 1.9011 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2091 2.1499 2.6704 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6195 2.6757 0.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9135 2.6938 1.5715 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0037 -0.4119 3.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2140 -1.9192 2.4809 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5940 -1.1592 2.7407 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5694 0.2437 2.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3860 -1.0137 0.1759 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8928 -1.9529 0.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3249 0.6175 -1.2639 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2361 -1.0247 -1.9327 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7552 2.3698 -3.4292 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7452 0.9397 -2.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6483 -0.4579 -2.6817 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3495 -0.7205 -2.3818 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6003 1.3876 -1.8600 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1455 1.8807 -1.1893 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9386 0.2352 -1.7976 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4054 0.1935 -2.5912 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5819 0.1457 -3.1731 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5175 -1.1682 -2.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6595 -1.1036 -1.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9529 1.6635 1.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9086 1.6787 0.2649 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3147 0.9233 1.5939 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 9 11 1 0 8 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 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 25 27 1 0 27 28 1 0 27 29 1 1 27 30 1 0 30 31 1 0 23 32 1 6 32 33 2 0 32 34 1 0 14 35 1 6 7 36 1 6 2 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 42 45 1 0 9 4 1 0 19 14 1 0 31 23 1 0 44 39 1 0 15 7 1 0 24 18 1 0 4 46 1 1 5 47 1 0 5 48 1 0 6 49 1 0 6 50 1 0 8 51 1 1 10 52 1 0 10 53 1 0 10 54 1 0 11 55 1 0 11 56 1 0 11 57 1 0 12 58 1 0 12 59 1 0 13 60 1 0 13 61 1 0 15 62 1 1 16 63 1 0 16 64 1 0 17 65 1 0 20 66 1 0 20 67 1 0 20 68 1 0 21 69 1 0 21 70 1 0 22 71 1 0 22 72 1 0 24 73 1 6 25 74 1 1 26 75 1 0 26 76 1 0 26 77 1 0 28 78 1 0 28 79 1 0 28 80 1 0 29 81 1 0 30 82 1 0 30 83 1 0 31 84 1 0 31 85 1 0 34 86 1 0 35 87 1 0 35 88 1 0 35 89 1 0 36 90 1 0 36 91 1 0 36 92 1 0 37 93 1 0 38 94 1 0 40 95 1 0 41 96 1 0 43 97 1 0 44 98 1 0 45 99 1 0 M END

Standard InCHIKey	QBVWEVAJCNZONP-JKGUJMMISA-N
Standard InCHI	InChI=1S/C39H54O6/c1-24-32-27-13-14-29-35(4)18-17-30(45-31(41)15-10-25-8-11-26(40)12-9-25)34(2,3)28(35)16-19-37(29,6)36(27,5)20-22-39(32,33(42)43)23-21-38(24,7)44/h8-13,15,24,28-30,32,40,44H,14,16-23H2,1-7H3,(H,42,43)/b15-10-/t24-,28+,29-,30+,32+,35+,36-,37-,38+,39-/m1/s1
SMILES	O=C(O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@@H](C)[C@@](C)(O)CC1)C(=O)O)C)C)/C=Cc1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.39	Volume:	666.047 ? Van der Waals volume.
Dense:	0.928	LogP:	5.188 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.142 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.186 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	35.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.179	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.036	Fsp³:	0.692
MCE-18:	165.879 ? 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:	0.967	Fluc inhibitor:	0.953 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.198 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.02 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.164	Promiscuous compounds:	0.077

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.575	MDCK Permeability:	-5.091
Pgp-inhibitor:	0.021	Pgp-substrate:	0.002
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):	0.002
20% Bioavailability (F20%):	0.864	30% Bioavailability (F30%):	0.235
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.943
Plasma Protein Binding (PPB):	98.264%	Volume Distribution (VD):	-0.291
Fu:	1.397% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.803	BCRP inhibitor:	0.003
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.066	CYP2C19-substrate:	0.009
CYP2C9-inhibitor:	0.045	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.025	CYP3A4-substrate:	0.637
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.958
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):

2.937

Half-life (T1/2):

1.11

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.064
Human Hepatotoxicity (H-HT):	0.693	Drug-induced Liver Injury (DILI):	0.086
AMES Toxicity:	0.158	Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.623	Skin Sensitization:	1.0
Carcinogencity:	0.378	Eye Corrosion:	0.023
Eye Irritation:	0.693	Respiratory Toxicity:	0.788
Drug-induced Neurotoxicity:	0.019	Ototoxicity:	0.234
Hematotoxicity:	0.039	Drug-induced Nephrotoxicity:	0.963
Genotoxicity:	0.457	RPMI-8226 Immunitoxicity:	0.026
A549 Cytotoxicity:	0.849	Hek293 Cytotoxicity:	0.654
BCF:	0.909 ? 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:	4.223 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.603 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.096 ? 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
NPO12610	Diospyros dendo	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441080]
NPO12610	Diospyros dendo	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12610	Diospyros dendo	Species	Ebenaceae	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
Inhibition	1

Activity Type	# Activity
Organism	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
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	Inhibition	=	62.0	%	PMID[22779787]

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 NPC172311 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	8275
0.1-0.2	36164
0.2-0.3	4546
0.3-0.4	683
0.4-0.5	126
0.5-0.6	38
0.6-0.7	21
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
0.7174	Intermediate Similarity	NPC477874
0.7053	Intermediate Similarity	NPC482052
0.7033	Intermediate Similarity	NPC485587
0.7021	Intermediate Similarity	NPC22676
0.6979	Remote Similarity	NPC304110
0.6979	Remote Similarity	NPC27518
0.6979	Remote Similarity	NPC611516
0.6957	Remote Similarity	NPC173569
0.6667	Remote Similarity	NPC610795
0.6633	Remote Similarity	NPC25491
0.6566	Remote Similarity	NPC479739
0.6566	Remote Similarity	NPC178093
0.6531	Remote Similarity	NPC479744
0.6531	Remote Similarity	NPC605663
0.65	Remote Similarity	NPC324798
0.65	Remote Similarity	NPC479742
0.6495	Remote Similarity	NPC477873
0.6214	Remote Similarity	NPC479740
0.6214	Remote Similarity	NPC479741
0.6082	Remote Similarity	NPC248287
0.6082	Remote Similarity	NPC234548
0.6078	Remote Similarity	NPC479747
0.6078	Remote Similarity	NPC479746
0.6038	Remote Similarity	NPC118033
0.6019	Remote Similarity	NPC482051
0.5962	Remote Similarity	NPC479745
0.5941	Remote Similarity	NPC198621
0.5941	Remote Similarity	NPC216940
0.5926	Remote Similarity	NPC53520
0.5918	Remote Similarity	NPC182249
0.5824	Remote Similarity	NPC485588
0.5769	Remote Similarity	NPC482049
0.5769	Remote Similarity	NPC482050
0.5758	Remote Similarity	NPC473591
0.5741	Remote Similarity	NPC481234
0.5741	Remote Similarity	NPC479431
0.573	Remote Similarity	NPC485589
0.5686	Remote Similarity	NPC488215
0.5648	Remote Similarity	NPC601567
0.5648	Remote Similarity	NPC606631
0.5588	Remote Similarity	NPC171007
0.5588	Remote Similarity	NPC190849
0.5577	Remote Similarity	NPC54627
0.5577	Remote Similarity	NPC249817
0.5524	Remote Similarity	NPC132126
0.5495	Remote Similarity	NPC481235
0.549	Remote Similarity	NPC8102
0.549	Remote Similarity	NPC66894
0.5484	Remote Similarity	NPC485586
0.5472	Remote Similarity	NPC475482
0.5429	Remote Similarity	NPC488214
0.5361	Remote Similarity	NPC485585
0.5354	Remote Similarity	NPC485882
0.5333	Remote Similarity	NPC262970
0.5294	Remote Similarity	NPC155192
0.5289	Remote Similarity	NPC488211
0.5288	Remote Similarity	NPC469447
0.5275	Remote Similarity	NPC120840
0.5234	Remote Similarity	NPC205392
0.5234	Remote Similarity	NPC105942
0.5155	Remote Similarity	NPC86257
0.5094	Remote Similarity	NPC101863
0.5079	Remote Similarity	NPC111466

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC172311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3837
0.1-0.2	5221
0.2-0.3	80
0.3-0.4	11
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