NPASS Compound

Natural Product: NPC469381

Natural Product ID	NPC469381
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JXHOOGQINSPTID-PVTPHBDQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44627500
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 94101 0 0 0 0 0 0 0 0999 V2000 7.7656 -2.2013 -1.9503 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4619 -1.5305 -1.7552 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3827 -0.3015 -1.2698 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6423 0.3929 -0.9233 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0717 0.3215 -1.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0586 1.4842 -0.6310 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8961 -0.2724 -1.3959 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5894 0.1427 -1.2867 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1803 0.2862 0.1896 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3214 -1.0788 0.8660 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5503 -1.2529 2.2920 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1711 -1.1503 1.8933 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3871 0.1351 1.7518 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1140 1.2582 2.5365 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6987 0.3904 0.3008 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0349 1.6458 -0.1487 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1556 1.7207 0.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5682 2.7081 1.4878 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9654 4.0447 1.7419 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7912 5.0881 1.4025 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2088 5.5045 0.1825 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8204 4.9174 -0.8296 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1401 6.6705 0.0161 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7639 2.2899 2.2165 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4174 2.9907 3.0414 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0694 0.9906 1.8553 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0703 0.5763 0.9984 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0498 0.0731 2.1271 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5707 -1.0450 2.9045 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2622 -2.0974 2.1631 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7689 -3.4892 2.3874 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6301 -4.6249 2.0325 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6240 -4.1111 0.9943 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2166 -3.1452 0.0469 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6164 -3.5313 -0.3959 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1508 -1.8751 0.7420 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1574 -0.6186 0.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2041 -0.6335 -1.2588 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5993 0.4149 -1.9214 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0367 1.5919 -1.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4583 0.4421 -3.3847 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9806 -0.3627 -4.1542 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9855 1.6366 -3.9706 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9281 1.8197 -5.3734 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1975 -1.9438 -1.9735 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7931 -2.0866 -3.0090 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3916 -3.0053 -1.2512 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4157 -4.1883 -1.9653 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6540 -2.1422 2.4568 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9612 1.1918 0.7729 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5692 -3.2855 -2.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3101 -1.8111 -2.8400 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4123 -2.1894 -1.0646 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5282 -2.0447 -2.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7468 0.5232 0.1872 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6995 1.4063 -1.3857 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5128 -0.1624 -1.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8958 -0.5541 -1.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5130 1.1662 -1.7411 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4511 -1.9042 0.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8897 -2.3080 2.5588 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2092 -0.5510 2.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5922 -2.0690 1.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9114 0.9034 3.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2581 2.1622 1.9573 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3374 1.5873 3.3093 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3817 -0.5169 -0.2611 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7425 2.4905 0.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1387 1.6101 -1.2274 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7806 4.1242 2.8625 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0494 4.1063 1.2598 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7403 6.7923 0.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5356 7.5426 -0.2279 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8032 6.4600 -0.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1218 0.9225 2.9070 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6823 -1.4376 3.4944 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2699 -0.7700 3.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9359 -3.6683 3.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7087 -4.4329 1.8779 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4399 -5.6357 2.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7475 -4.7154 0.7710 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8377 -4.5982 -0.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7605 -3.4941 -1.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3464 -2.8253 0.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7784 1.4774 -0.3905 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5620 2.5353 -1.4023 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9417 1.8533 -1.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9980 1.3156 -5.7152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7446 2.9216 -5.5211 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8330 1.4695 -5.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3918 -2.6612 -0.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3467 -4.9612 -1.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7399 -1.7673 3.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5496 0.9525 1.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 18 24 1 0 24 25 2 0 24 26 1 0 27 26 1 1 27 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 34 35 1 6 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 39 41 1 0 41 42 2 0 41 43 1 0 43 44 1 0 38 45 1 0 45 46 2 0 45 47 1 0 47 48 1 0 30 49 1 1 9 50 1 1 15 9 1 0 27 17 1 0 36 30 1 0 12 10 1 0 28 13 1 0 33 31 1 0 47 34 1 0 37 27 1 0 1 51 1 0 1 52 1 0 1 53 1 0 2 54 1 0 4 55 1 0 4 56 1 0 4 57 1 0 8 58 1 0 8 59 1 0 10 60 1 6 11 61 1 0 11 62 1 0 12 63 1 6 14 64 1 0 14 65 1 0 14 66 1 0 15 67 1 6 16 68 1 0 16 69 1 0 19 70 1 0 19 71 1 0 23 72 1 0 23 73 1 0 23 74 1 0 28 75 1 1 29 76 1 0 29 77 1 0 31 78 1 1 32 79 1 0 32 80 1 0 33 81 1 6 35 82 1 0 35 83 1 0 35 84 1 0 40 85 1 0 40 86 1 0 40 87 1 0 44 88 1 0 44 89 1 0 44 90 1 0 47 91 1 1 48 92 1 0 49 93 1 0 50 94 1 0 M END

Standard InCHIKey	JXHOOGQINSPTID-PVTPHBDQSA-N
Standard InCHI	InChI=1S/C38H44O12/c1-8-15(2)31(42)49-14-37(46)23-9-20(23)34(5)24(37)11-19-18(13-48-17(4)39)33(44)50-38(19)25(34)12-36(45)22-10-21(22)35(6)29(36)27(38)26(28(40)30(35)41)16(3)32(43)47-7/h8,20-25,30,41,45-46H,9-14H2,1-7H3/b15-8+,26-16-/t20-,21-,22+,23+,24-,25+,30+,34+,35+,36+,37+,38+/m1/s1
SMILES	C/C=C(C)/C(=O)OC[C@@]1([C@H]2C[C@H]2[C@@]2(C)[C@H]1CC1=C(COC(=O)C)C(=O)O[C@@]31[C@H]2C[C@@]1([C@H]2C[C@H]2[C@@]2(C)C1=C3/C(=C(C)/C(=O)OC)/C(=O)[C@@H]2O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	692.28	Volume:	679.107 ? Van der Waals volume.
Dense:	1.019	LogP:	1.047 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.43 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.756 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	38.0
TPSA:	182.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	3.0	Rings:	8.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.21	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.79	Fsp³:	0.658
MCE-18:	203.46 ? 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:	0.498	Fluc inhibitor:	0.015 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.526 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.217	Promiscuous compounds:	0.496

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.176	MDCK Permeability:	-4.834
Pgp-inhibitor:	0.003	Pgp-substrate:	0.843
PAMPA:	0.995 ? 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):	0.03
20% Bioavailability (F20%):	0.992	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05	MRP1:	0.998
Plasma Protein Binding (PPB):	72.761%	Volume Distribution (VD):	-0.189
Fu:	22.876% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.076
BSEP inhibitor:	0.907

ADMET: Metabolism

CYP1A2-inhibitor:	0.056	CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.531
CYP3A4-inhibitor:	0.973	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.989 ? 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):

2.219

Half-life (T1/2):

1.743

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.049
Human Hepatotoxicity (H-HT):	0.904	Drug-induced Liver Injury (DILI):	0.833
AMES Toxicity:	0.892	Rat Oral Acute Toxicity:	0.426
Maximum Recommended Daily Dose:	0.899	Skin Sensitization:	1.0
Carcinogencity:	0.967	Eye Corrosion:	0.0
Eye Irritation:	0.015	Respiratory Toxicity:	0.235
Drug-induced Neurotoxicity:	0.1	Ototoxicity:	0.7
Hematotoxicity:	0.864	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.335
A549 Cytotoxicity:	0.345	Hek293 Cytotoxicity:	0.438
BCF:	0.418 ? 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:	3.601 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.768 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.932 ? 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
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27997206]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	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	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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	25000.0	nM	PMID[27997206]

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 NPC469381 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	21281
0.1-0.2	27949
0.2-0.3	567
0.3-0.4	10
0.4-0.5	23
0.5-0.6	17
0.6-0.7	7
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
0.8427	Intermediate Similarity	NPC213697
0.7363	Intermediate Similarity	NPC242451
0.7333	Intermediate Similarity	NPC469674
0.6465	Remote Similarity	NPC192334
0.6465	Remote Similarity	NPC60150
0.625	Remote Similarity	NPC254823
0.6238	Remote Similarity	NPC327664
0.6238	Remote Similarity	NPC476097
0.6186	Remote Similarity	NPC35109
0.6082	Remote Similarity	NPC134902
0.5922	Remote Similarity	NPC481183
0.5825	Remote Similarity	NPC279992
0.5825	Remote Similarity	NPC476824
0.5758	Remote Similarity	NPC25887
0.5755	Remote Similarity	NPC100347
0.5714	Remote Similarity	NPC470426
0.5648	Remote Similarity	NPC486801
0.5524	Remote Similarity	NPC476825
0.5455	Remote Similarity	NPC15095
0.5392	Remote Similarity	NPC299570
0.5368	Remote Similarity	NPC486813
0.5294	Remote Similarity	NPC486811
0.5294	Remote Similarity	NPC220757
0.5234	Remote Similarity	NPC34963
0.5234	Remote Similarity	NPC186637
0.5091	Remote Similarity	NPC486810
0.5045	Remote Similarity	NPC290020

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7313
0.1-0.2	1802
0.2-0.3	35
0.3-0.4	0
0.4-0.5	0
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