NPASS Compound

Natural Product: NPC541905

Natural Product ID	NPC541905
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Myriceric acid B
IUPAC Name	(4~{a}~{S},6~{a}~{R},6~{a}~{R},6~{b}~{R},8~{a}~{R},10~{S},12~{a}~{R},14~{b}~{S})-6~{a}-[[(~{E})-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-10-hydroxy-2,2,6~{b},9,9,12~{a}-hexamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-4~{a}-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: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 100105 0 0 0 0 0 0 0 0999 V2000 -1.2636 6.2996 -1.3856 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 5.2777 -0.7708 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7614 5.0552 -1.8230 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3933 5.9290 0.4211 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3778 4.9019 0.9089 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6317 3.8082 1.6056 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4997 4.2590 3.0262 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9854 3.6167 3.9911 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1711 5.4110 3.3136 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5304 2.5969 1.6669 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8271 1.3250 2.0652 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2583 0.9784 1.0293 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4753 1.0019 -0.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5375 0.0750 -0.2305 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4002 -0.1612 -1.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2759 0.4607 -2.3375 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.1334 -1.1261 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3142 -1.3838 -2.1127 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3939 -2.3480 -2.0221 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6597 -3.1037 -0.9084 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7215 -4.0139 -0.8998 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5444 -4.1998 -1.9866 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5997 -5.1032 -1.9800 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2770 -3.4404 -3.1053 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0946 -3.6078 -4.2219 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2357 -2.5439 -3.1217 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1556 2.1441 1.2201 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3697 1.9511 1.6163 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9973 0.6397 1.9166 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3377 -0.3183 0.9392 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1045 -1.5727 0.7676 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5808 -2.2365 2.0232 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3599 -1.2312 -0.0385 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1233 -2.4342 -0.4878 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3260 -3.4722 -1.1791 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0635 -4.6779 -1.1486 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9560 -3.7052 -0.6253 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1091 -4.1788 -1.8248 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9954 -4.8701 0.3229 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3000 -2.4827 -0.1277 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9681 -2.7796 0.5155 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2309 -1.4491 0.4474 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8912 -0.3557 1.2557 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6086 -0.7289 2.7060 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7011 3.5485 0.9835 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9567 4.0000 -0.4056 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7329 5.7763 -2.2485 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6122 7.1030 -1.7979 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9747 6.7004 -0.6707 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6396 5.6850 -1.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3809 5.2706 -2.8452 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1052 4.0048 -1.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3656 6.1513 1.1866 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9143 6.8666 0.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0746 5.4126 1.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9763 4.4894 0.0387 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3318 5.8133 4.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2607 2.7531 2.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2336 2.4985 0.8225 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5940 0.5439 2.1334 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3737 1.5606 3.0577 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1984 0.7738 -1.1461 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9559 1.9339 -0.5561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5706 -1.6626 -0.2044 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1830 -0.8267 -3.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0444 -3.0043 -0.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9366 -4.6121 -0.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5070 -6.0348 -1.5832 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0450 -2.9460 -4.9787 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0890 -1.9777 -4.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0522 2.8192 1.7625 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1080 0.6733 1.7824 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8547 0.3475 2.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4159 0.2235 -0.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0080 -3.1492 2.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6517 -2.5805 1.9798 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5716 -1.5046 2.8538 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0776 -0.6178 0.5589 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0525 -0.6750 -0.9728 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8876 -2.0473 -1.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7336 -2.9222 0.2959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2777 -3.2129 -2.2777 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0333 -4.4479 -1.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7676 -4.8253 -2.4425 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8276 -3.3074 -2.4459 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2584 -4.7901 -1.5042 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9308 -4.9009 0.9344 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0754 -5.7965 -0.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0777 -5.0018 0.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0597 -1.8625 -1.0207 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -3.2313 1.4912 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4217 -3.4481 -0.1805 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2921 -1.1825 -0.6249 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7803 -1.7037 0.8172 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1547 -1.6460 3.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9065 0.0508 3.3987 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4610 -1.0236 2.7426 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3805 4.2556 1.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0790 4.2163 -0.4806 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8251 3.2704 -1.2177 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 1 7 8 2 0 7 9 1 0 6 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 1 0 24 26 2 0 12 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 1 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 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 27 45 1 0 45 46 1 0 46 2 1 0 45 6 1 0 43 12 1 0 26 19 1 0 43 30 1 0 40 31 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 9 57 1 0 10 58 1 0 10 59 1 0 11 60 1 0 11 61 1 0 13 62 1 0 13 63 1 0 17 64 1 0 18 65 1 0 20 66 1 0 21 67 1 0 23 68 1 0 25 69 1 0 26 70 1 0 28 71 1 0 29 72 1 0 29 73 1 0 30 74 1 6 32 75 1 0 32 76 1 0 32 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 35 82 1 6 36 83 1 0 38 84 1 0 38 85 1 0 38 86 1 0 39 87 1 0 39 88 1 0 39 89 1 0 40 90 1 6 41 91 1 0 41 92 1 0 42 93 1 0 42 94 1 0 44 95 1 0 44 96 1 0 44 97 1 0 45 98 1 1 46 99 1 0 46100 1 0 M END

Standard InCHIKey	IZCSLJUDQLFLNO-YYGQYJBBSA-N
Standard InCHI	InChI=1S/C39H54O7/c1-34(2)17-18-38(33(44)45)19-20-39(23-46-32(43)12-8-24-7-10-27(40)28(41)21-24)25(26(38)22-34)9-11-30-36(5)15-14-31(42)35(3,4)29(36)13-16-37(30,39)6/h7-10,12,21,26,29-31,40-42H,11,13-20,22-23H2,1-6H3,(H,44,45)/b12-8+/t26-,29-,30+,31-,36-,37+,38-,39-/m0/s1
SMILES	CC1(C)CC[C@]2(C(=O)O)CC[C@]3(COC(=O)/C=C/C4=CC=C(O)C(O)=C4)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.39	Volume:	674.838 ? Van der Waals volume.
Dense:	0.94	LogP:	4.402 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.672 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.463 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	124.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.112	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.984	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:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.992	Fluc inhibitor:	0.687 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.055 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.054 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.132	Promiscuous compounds:	0.083

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.554	MDCK Permeability:	-5.066
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
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):	0.004
20% Bioavailability (F20%):	0.994	30% Bioavailability (F30%):	0.82
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061	MRP1:	0.771
Plasma Protein Binding (PPB):	97.175%	Volume Distribution (VD):	-0.488
Fu:	2.456% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.002
BSEP inhibitor:	0.529

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.059	CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.935
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.866
HLM stability:	0.146 ? 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):

3.861

Half-life (T1/2):

1.42

ADMET: Toxicity

hERG Blockers:	0.083	hERG Blockers (10um):	0.15
Human Hepatotoxicity (H-HT):	0.687	Drug-induced Liver Injury (DILI):	0.658
AMES Toxicity:	0.536	Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.797	Skin Sensitization:	0.998
Carcinogencity:	0.808	Eye Corrosion:	0.0
Eye Irritation:	0.146	Respiratory Toxicity:	0.727
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.88
Hematotoxicity:	0.164	Drug-induced Nephrotoxicity:	0.742
Genotoxicity:	0.937	RPMI-8226 Immunitoxicity:	0.021
A549 Cytotoxicity:	0.772	Hek293 Cytotoxicity:	0.287
BCF:	1.068 ? 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:	4.388 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.93 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.385 ? 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
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	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 NPC541905 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	7731
0.1-0.2	36694
0.2-0.3	4656
0.3-0.4	588
0.4-0.5	127
0.5-0.6	38
0.6-0.7	7
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9059	High Similarity	NPC262970
0.837	Intermediate Similarity	NPC206232
0.837	Intermediate Similarity	NPC14515
0.8022	Intermediate Similarity	NPC606782
0.7475	Intermediate Similarity	NPC53520
0.7419	Intermediate Similarity	NPC198621
0.7419	Intermediate Similarity	NPC216940
0.734	Intermediate Similarity	NPC54627
0.734	Intermediate Similarity	NPC249817
0.6907	Remote Similarity	NPC132126
0.6832	Remote Similarity	NPC310729
0.6832	Remote Similarity	NPC150310
0.6667	Remote Similarity	NPC475482
0.6392	Remote Similarity	NPC475627
0.6327	Remote Similarity	NPC271494
0.6117	Remote Similarity	NPC475311
0.5859	Remote Similarity	NPC43353
0.5825	Remote Similarity	NPC605663
0.58	Remote Similarity	NPC18982
0.5784	Remote Similarity	NPC22676
0.5784	Remote Similarity	NPC488215
0.5747	Remote Similarity	NPC480946
0.5747	Remote Similarity	NPC130577
0.5747	Remote Similarity	NPC142415
0.5747	Remote Similarity	NPC102683
0.5747	Remote Similarity	NPC198664
0.5455	Remote Similarity	NPC601567
0.5455	Remote Similarity	NPC606631
0.5421	Remote Similarity	NPC479747
0.5421	Remote Similarity	NPC479746
0.5421	Remote Similarity	NPC482049
0.5421	Remote Similarity	NPC482050
0.5385	Remote Similarity	NPC171007
0.5385	Remote Similarity	NPC190849
0.537	Remote Similarity	NPC482051
0.537	Remote Similarity	NPC610795
0.5321	Remote Similarity	NPC479745
0.5273	Remote Similarity	NPC473680
0.5273	Remote Similarity	NPC479740
0.5273	Remote Similarity	NPC479741
0.5263	Remote Similarity	NPC474727
0.5238	Remote Similarity	NPC475457
0.5185	Remote Similarity	NPC487492
0.514	Remote Similarity	NPC487491
0.5091	Remote Similarity	NPC473773
0.5091	Remote Similarity	NPC475579
0.5054	Remote Similarity	NPC228784
0.5054	Remote Similarity	NPC324341
0.5054	Remote Similarity	NPC298554
0.5054	Remote Similarity	NPC29765
0.5054	Remote Similarity	NPC601810
0.5047	Remote Similarity	NPC477873
0.5045	Remote Similarity	NPC475454
0.5045	Remote Similarity	NPC473579

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC541905 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3224
0.1-0.2	5826
0.2-0.3	95
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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	Drug ID	Developmental Stage
0.8022	Intermediate Similarity	NPD8166	Discontinued

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