NPASS Compound

Natural Product: NPC186637

Natural Product ID	NPC186637
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NCEFZVURTXZBJM-ISHMMZPFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	25180764
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 97105 0 0 0 0 0 0 0 0999 V2000 6.0983 -0.4127 -3.8727 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3382 -0.2861 -2.5984 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4783 0.7275 -1.7787 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3659 1.8807 -1.9380 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7378 3.1365 -1.9841 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9254 3.6289 -1.0028 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7325 2.8738 0.0028 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2400 4.9509 -0.9841 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1815 4.9169 0.1638 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2538 3.8474 -0.2440 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3143 3.4468 -1.4536 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3099 3.2189 0.5698 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5493 2.2166 -0.1033 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3432 1.4377 0.7601 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4275 0.1752 0.6671 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3434 -0.6289 -0.2615 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6929 -1.9322 0.3993 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3611 -1.9629 1.8776 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0272 -0.9460 2.7231 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8216 -3.3410 2.2116 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1824 -3.7111 2.6128 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9371 -3.6582 1.1519 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1213 -2.3006 0.4511 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8122 -2.5095 -0.8544 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6878 -1.4015 -1.1171 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4153 -1.3974 -2.2782 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3029 -2.3437 -3.0814 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9348 -1.4755 1.2244 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1351 -1.7244 1.9556 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9030 -2.7619 1.2181 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3422 -2.4492 -0.1426 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8293 -1.2552 -0.3098 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8610 -0.3879 0.8713 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3817 0.9000 0.4606 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1958 1.5999 1.2220 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6431 2.9384 0.6281 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7242 1.2491 2.5128 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5005 0.2014 3.1343 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5693 2.1608 3.1403 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1251 1.8697 4.4217 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9689 1.3860 -0.8818 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7947 2.6141 -1.0101 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7746 0.4175 -2.0288 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3438 -0.9048 -1.5952 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8777 -0.8400 -1.5719 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9416 -2.0866 -2.4420 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6563 -3.3470 -2.1055 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3690 -3.1205 -1.4524 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6262 0.9505 -3.0398 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4749 -0.3544 1.5164 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6147 0.6462 2.4969 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1119 1.8149 1.9398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2912 3.0000 2.3821 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5362 0.0743 -4.6813 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1338 -0.0305 -3.7492 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2206 -1.4929 -4.1235 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8638 0.7217 -0.8621 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9981 1.7991 -2.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1001 1.8468 -1.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7045 5.0978 -1.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9092 5.7860 -0.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6417 5.8846 0.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6842 4.7713 1.1186 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0713 2.7928 -0.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2737 1.6533 -0.6979 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2336 -0.8600 -1.1539 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3095 -0.1983 -0.6078 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1687 -2.7901 -0.0674 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4842 -0.0896 2.2447 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8561 -1.3834 3.3643 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2931 -0.6411 3.5361 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0496 -4.0819 2.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9638 -3.0297 2.9699 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3244 -4.7362 3.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6880 -4.5138 0.5257 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0564 -2.6008 -1.6556 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3751 -3.4630 -0.8145 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7934 -1.9957 1.3358 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4143 -1.8652 3.0545 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2542 -3.6951 1.0599 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8111 -3.1036 1.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5153 -0.8792 1.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0273 2.7925 -0.4041 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8682 3.6973 0.7413 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5198 3.2953 1.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9544 2.5563 4.5797 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3391 1.9448 5.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4496 0.8034 4.3809 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7574 0.3591 -2.3813 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2982 -1.3376 -2.4500 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2246 -1.3843 -0.6700 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1976 0.2098 -1.4527 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5261 -1.9909 -3.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7518 -4.1747 -2.8575 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5709 -3.2858 -1.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 -3.5493 -1.8594 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5629 0.4195 -3.8651 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 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 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 2 0 23 28 1 1 18 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 34 41 1 0 41 42 2 0 41 43 1 0 43 44 1 0 44 45 1 1 44 46 1 0 46 47 1 0 47 48 1 0 43 49 1 0 33 50 1 0 50 51 1 1 51 52 1 0 52 53 2 0 26 2 1 0 50 29 1 0 52 14 1 0 50 15 1 0 23 17 1 0 48 31 1 0 22 20 1 0 44 32 1 0 48 46 1 0 1 54 1 0 1 55 1 0 1 56 1 0 3 57 1 0 4 58 1 0 4 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 13 64 1 0 13 65 1 0 16 66 1 0 16 67 1 0 17 68 1 6 19 69 1 0 19 70 1 0 19 71 1 0 20 72 1 1 21 73 1 0 21 74 1 0 22 75 1 6 24 76 1 0 24 77 1 0 28 78 1 0 29 79 1 1 30 80 1 0 30 81 1 0 33 82 1 1 36 83 1 0 36 84 1 0 36 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 43 89 1 6 45 90 1 0 45 91 1 0 45 92 1 0 46 93 1 6 47 94 1 0 47 95 1 0 48 96 1 6 49 97 1 0 M END

Standard InCHIKey	NCEFZVURTXZBJM-ISHMMZPFSA-N
Standard InCHI	InChI=1S/C40H44O13/c1-16-8-9-50-27(41)6-7-28(42)51-14-20-22-13-25-37(3,23-12-24(23)39(25,48)15-52-34(16)45)26-11-19-18-10-21(18)38(4)30(19)31(40(22,26)53-36(20)47)29(32(43)33(38)44)17(2)35(46)49-5/h8,18,21,23-26,31,33,44,48H,6-7,9-15H2,1-5H3/b16-8+,29-17+/t18-,21-,23-,24+,25-,26+,31+,33+,37+,38+,39+,40+/m1/s1
SMILES	C/C/1=CCOC(=O)CCC(=O)OCC2=C3C[C@@H]4[C@](C)([C@@H]5C[C@@H]5[C@]4(COC1=O)O)[C@@H]1CC4=C5[C@H](/C(=C(/C)C(=O)OC)/C(=O)[C@@H]([C@@]5(C)[C@@H]5C[C@H]45)O)[C@]31OC2=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	732.28	Volume:	711.296 ? Van der Waals volume.
Dense:	1.03	LogP:	1.226 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.625 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.176 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	52.0
TPSA:	189.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	2.0	Rings:	9.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.173	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.997	Fsp³:	0.65
MCE-18:	218.182 ? 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:	0.628	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.84 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.294 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.173	Promiscuous compounds:	0.636

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.374	MDCK Permeability:	-4.947
Pgp-inhibitor:	0.002	Pgp-substrate:	0.311
PAMPA:	0.917 ? 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):	0.0
20% Bioavailability (F20%):	0.859	30% Bioavailability (F30%):	0.459
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.419	MRP1:	1.0
Plasma Protein Binding (PPB):	69.065%	Volume Distribution (VD):	0.053
Fu:	29.716% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.986
OATP1B3 inhibitor:	0.985	BCRP inhibitor:	0.001
BSEP inhibitor:	0.907

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.362
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.387
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	1.0 ? 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):

3.254

Half-life (T1/2):

1.764

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.084
Human Hepatotoxicity (H-HT):	0.973	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.974	Rat Oral Acute Toxicity:	0.711
Maximum Recommended Daily Dose:	0.997	Skin Sensitization:	1.0
Carcinogencity:	0.996	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.083
Drug-induced Neurotoxicity:	0.526	Ototoxicity:	0.815
Hematotoxicity:	0.994	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.794
A549 Cytotoxicity:	0.932	Hek293 Cytotoxicity:	0.91
BCF:	0.388 ? 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:	3.629 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.725 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.839 ? 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
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053511]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22372956]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588583]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724564]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21178	Chloranthus serratus	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
Activity	1
IC50	1

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	Activity	=	66.5	%	PMID[30724564]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	25500.0	nM	PMID[30724564]

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 NPC186637 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	22698
0.1-0.2	26893
0.2-0.3	212
0.3-0.4	6
0.4-0.5	11
0.5-0.6	14
0.6-0.7	5
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC34963
0.8696	High Similarity	NPC290020
0.8409	Intermediate Similarity	NPC35109
0.8333	Intermediate Similarity	NPC58029
0.8152	Intermediate Similarity	NPC241935
0.8152	Intermediate Similarity	NPC486803
0.7979	Intermediate Similarity	NPC486797
0.7979	Intermediate Similarity	NPC164241
0.7979	Intermediate Similarity	NPC469673
0.7812	Intermediate Similarity	NPC486810
0.7802	Intermediate Similarity	NPC299570
0.7753	Intermediate Similarity	NPC15095
0.75	Intermediate Similarity	NPC486811
0.75	Intermediate Similarity	NPC220757
0.734	Intermediate Similarity	NPC196921
0.72	Intermediate Similarity	NPC279478
0.7172	Intermediate Similarity	NPC486798
0.7065	Intermediate Similarity	NPC275236
0.6947	Remote Similarity	NPC486799
0.6875	Remote Similarity	NPC59488
0.6804	Remote Similarity	NPC19772
0.6408	Remote Similarity	NPC213697
0.6	Remote Similarity	NPC486809
0.5648	Remote Similarity	NPC24599
0.5556	Remote Similarity	NPC192334
0.5556	Remote Similarity	NPC60150
0.551	Remote Similarity	NPC263046
0.5364	Remote Similarity	NPC470427
0.5364	Remote Similarity	NPC486808
0.5347	Remote Similarity	NPC17938
0.5263	Remote Similarity	NPC309497
0.5263	Remote Similarity	NPC611150
0.5234	Remote Similarity	NPC469381
0.5225	Remote Similarity	NPC327664
0.5225	Remote Similarity	NPC481183
0.5225	Remote Similarity	NPC476097
0.5044	Remote Similarity	NPC470426

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC186637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7344
0.1-0.2	1786
0.2-0.3	20
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