NPASS Compound

Natural Product: NPC49362

Natural Product ID	NPC49362
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MWNYEDALQAWIQT-VXDKBRHYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	72737187
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 225236 0 0 0 0 0 0 0 0999 V2000 -6.0728 3.6869 2.7449 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6438 2.3647 2.2797 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6679 2.0447 1.0553 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.1498 0.8735 0.3958 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5504 0.5135 0.7506 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7942 -0.9369 0.7321 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9084 -1.7664 -0.1510 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5446 -2.0213 -1.5231 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4983 -0.8578 -2.2693 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0458 -1.0107 -3.5439 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3574 -0.2678 -3.5764 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2701 1.1476 -4.0230 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8476 1.4978 -4.3465 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1583 0.4335 -5.1297 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1800 -0.7821 -4.5519 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0983 1.7554 -3.2053 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6733 1.9823 -2.9736 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8007 2.7447 -3.3031 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.9126 2.3960 -2.3398 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.1695 3.1813 -2.7147 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.8055 4.6459 -2.7120 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.3388 4.8116 -2.4007 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5389 4.0939 -3.2604 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.1809 5.2909 -3.8766 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.1508 2.8971 -1.7453 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.1696 1.0282 -2.4770 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3028 -0.9405 -4.3566 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6285 -1.3877 -0.2331 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2301 -0.2624 0.5270 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9553 0.0983 0.0666 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9246 -0.2481 0.9855 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3372 -1.4840 0.3953 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8999 -1.7256 0.5908 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0719 -0.4597 0.2396 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3082 -0.1762 -1.1838 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5420 0.5570 1.2128 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6505 1.7427 1.2544 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7571 1.3140 1.6487 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2953 0.2522 0.7252 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4924 0.8883 -0.6276 C 0 0 0 0 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0 0 0 -7.0143 0.5471 3.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 20 25 1 0 19 26 1 0 11 27 1 0 7 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 1 0 37 38 1 0 38 39 1 0 39 40 1 6 39 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 47 49 1 0 47 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 1 54 57 1 0 53 58 1 0 52 59 1 6 59 60 2 0 59 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 2 0 69 71 1 0 66 72 1 0 65 73 1 0 64 74 1 0 63 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 83 86 1 0 86 87 1 0 83 88 1 6 82 89 1 0 78 90 1 0 90 91 1 0 78 92 1 6 77 93 1 0 36 94 1 0 94 95 1 0 94 96 1 0 6 97 1 0 97 98 1 0 98 99 1 0 99100 1 0 100101 1 0 101102 1 0 102103 1 0 103104 1 0 102105 1 0 101106 1 0 100107 1 0 99108 1 0 5109 1 0 2110 1 0 29 4 1 0 94 31 1 0 105 98 1 0 15 10 1 0 23 18 1 0 41 34 1 0 55 44 1 0 72 62 1 0 91 76 1 0 55 39 1 0 87 81 1 0 52 45 1 0 1111 1 0 1112 1 0 1113 1 0 4114 1 6 5115 1 1 6116 1 6 7117 1 1 8118 1 0 8119 1 0 10120 1 1 11121 1 1 12122 1 6 13123 1 6 14124 1 0 14125 1 0 16126 1 0 18127 1 6 19128 1 1 20129 1 6 21130 1 1 22131 1 0 22132 1 0 24133 1 0 25134 1 0 26135 1 0 27136 1 0 29137 1 1 31138 1 1 32139 1 0 32140 1 0 33141 1 0 33142 1 0 35143 1 0 35144 1 0 35145 1 0 36146 1 1 37147 1 0 37148 1 0 38149 1 0 38150 1 0 40151 1 0 40152 1 0 40153 1 0 41154 1 1 42155 1 0 42156 1 0 43157 1 0 45158 1 6 46159 1 0 46160 1 0 48161 1 0 48162 1 0 48163 1 0 49164 1 0 49165 1 0 49166 1 0 50167 1 0 50168 1 0 51169 1 0 51170 1 0 53171 1 6 54172 1 6 56173 1 0 56174 1 0 56175 1 0 57176 1 0 58177 1 0 62178 1 1 63179 1 1 64180 1 1 65181 1 6 66182 1 6 67183 1 0 67184 1 0 71185 1 0 71186 1 0 71187 1 0 73188 1 0 74189 1 0 76190 1 6 77191 1 1 79192 1 0 79193 1 0 81194 1 6 82195 1 1 84196 1 0 84197 1 0 85198 1 0 86199 1 0 86200 1 0 88201 1 0 89202 1 0 90203 1 0 90204 1 0 92205 1 0 93206 1 0 95207 1 0 95208 1 0 95209 1 0 96210 1 0 96211 1 0 96212 1 0 98213 1 6 99214 1 1 100215 1 6 101216 1 1 102217 1 6 103218 1 0 103219 1 0 104220 1 0 106221 1 0 107222 1 0 108223 1 0 109224 1 0 110225 1 0 M END

Standard InCHIKey	MWNYEDALQAWIQT-VXDKBRHYSA-N
Standard InCHI	InChI=1S/C72H115NO37/c1-28(76)73-40-44(83)51(108-60-48(87)45(84)42(81)34(19-74)103-60)36(23-99-58-49(88)50(33(79)21-97-58)107-59-47(86)41(80)32(78)20-98-59)105-57(40)106-39-13-14-67(7)37(66(39,5)6)12-15-68(8)38(67)11-10-30-31-18-65(3,4)16-17-72(31,54(90)53(89)69(30,68)9)64(93)110-61-52(46(85)43(82)35(104-61)22-96-29(2)77)109-63-56(92)71(95,27-102-63)26-101-62-55(91)70(94,24-75)25-100-62/h10,31-63,74-75,78-92,94-95H,11-27H2,1-9H3,(H,73,76)/t31-,32+,33-,34+,35+,36+,37-,38+,39-,40+,41-,42+,43+,44+,45-,46-,47+,48+,49+,50-,51+,52+,53-,54+,55-,56-,57-,58-,59-,60-,61-,62-,63-,67-,68+,69-,70+,71+,72+/m0/s1
SMILES	CC(=N[C@@H]1[C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@H](CO2)O)O[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O)O[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4([C@@H]([C@@H]([C@@]32C)O)O)C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)C)O2)O)O)O[C@H]2[C@@H]([C@@](CO[C@H]3[C@@H]([C@@](CO)(CO3)O)O)(CO2)O)O)C1(C)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1585.71	Volume:	1476.879 ? Van der Waals volume.
Dense:	1.074	LogP:	0.196 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.071 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.153 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	23.0	Rigid Bonds:	69.0
TPSA:	589.55 ? Topological Polar Surface Area.	H-Bond Acceptor:	38.0
H-Bond Donor:	20.0	Rings:	12.0
Heavy Atoms:	38.0

MedChem Properties

QED Drug-Likeness Score:	0.017	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.503	Fsp³:	0.931
MCE-18:	267.971 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.669	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.157	Promiscuous compounds:	0.532

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.952	MDCK Permeability:	-5.018
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.973
20% Bioavailability (F20%):	0.736	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.007
Plasma Protein Binding (PPB):	49.726%	Volume Distribution (VD):	-0.356
Fu:	28.698% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.001 ? 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):

-1.223

Half-life (T1/2):

4.274

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.998	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.999	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.015	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.631	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.939	RPMI-8226 Immunitoxicity:	0.387
A549 Cytotoxicity:	0.946	Hek293 Cytotoxicity:	0.402
BCF:	0.382 ? 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:	3.354 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.188 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.797 ? 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
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754604]
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12165300]
NPO19240	Ligularia cymbulifera	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[16643057]
NPO8080	Sarcophyton elegans	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18004813]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	Roots	Simao city, Yunnan Province, China	2007-MAY	PMID[19374435]
NPO19832	Gambierdiscus toxicus	Species	Goniodomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21250701]
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[21458279]
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	Vietnamese soft coral	n.a.	PMID[21507644]
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9222055]
NPO18599	Pangium edule	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17749	Jackiella javanica	Species	Jackiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8080	Sarcophyton elegans	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18260	Eremanthus seidelii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18041	Cladrastis platycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4499	Aglaia formosana	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15119	Aphis graminum	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19631	Aphis pini	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18925	Artemisia rehan	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15437	Aspergillus desertorum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18163	Aulosira fertilissima	Species	Fortieaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11083	Avrainvillea longicaulis	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16132	Bryum argenteum	Species	Bryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12860	Clione antarctica	Species	Clionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19370	Coprosma areolata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19306	Cortinarius orellanus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16316	Cylindrospermum muscicola	Species	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14249	Diplodia natalensis	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19010	Elephantopus hirtiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16978	Entada phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16776	Euphorbia amygdaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19832	Gambierdiscus toxicus	Species	Goniodomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26532	Gmelina asiatica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13344	Helichrysum cephaloideum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13727	Hemionitis japonica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17222	Hesperis matronalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15481	Hypericum balearicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17350	Jatropha macrorhiza	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19240	Ligularia cymbulifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18839	Lilium umbellatum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21660	Magnolia montana	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19086	Nematolepis phebalioides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19571	Oreopteris quelpaertensis	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18345	Phora velutina	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19706	Polyzonium rosalbum	Species	Polyzoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2354	Rhizobium leguminosarum	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17894	Rhus vulgaris	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14214	Sedum obtuso-lineare	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18672	Senecio adenophyllus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19168	Solidago flexicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22636	Sterculia foetida	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18422	Stizolobium deeringianum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17490	Trichophyton mentagrophytes	Species	Arthrodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14715	Trollius chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15786	Umbilicaria esculenta	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19766	Viguiera linearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Leaf Diffusate	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18599	Pangium edule	Species	Achariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14715	Trollius chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15786	Umbilicaria esculenta	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16978	Entada phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15786	Umbilicaria esculenta	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14715	Trollius chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22636	Sterculia foetida	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17749	Jackiella javanica	Species	Jackiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16978	Entada phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22636	Sterculia foetida	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16978	Entada phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26532	Gmelina asiatica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19240	Ligularia cymbulifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8080	Sarcophyton elegans	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18163	Aulosira fertilissima	Species	Fortieaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19168	Solidago flexicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16978	Entada phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16316	Cylindrospermum muscicola	Species	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19010	Elephantopus hirtiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15119	Aphis graminum	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18839	Lilium umbellatum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18599	Pangium edule	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14214	Sedum obtuso-lineare	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18925	Artemisia rehan	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17350	Jatropha macrorhiza	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2354	Rhizobium leguminosarum	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18345	Phora velutina	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18260	Eremanthus seidelii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19571	Oreopteris quelpaertensis	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14715	Trollius chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19706	Polyzonium rosalbum	Species	Polyzoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19832	Gambierdiscus toxicus	Species	Goniodomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21660	Magnolia montana	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15437	Aspergillus desertorum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14249	Diplodia natalensis	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15481	Hypericum balearicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16776	Euphorbia amygdaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19631	Aphis pini	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13727	Hemionitis japonica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11083	Avrainvillea longicaulis	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17222	Hesperis matronalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19306	Cortinarius orellanus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15786	Umbilicaria esculenta	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17749	Jackiella javanica	Species	Jackiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18672	Senecio adenophyllus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17490	Trichophyton mentagrophytes	Species	Arthrodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22636	Sterculia foetida	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4499	Aglaia formosana	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13344	Helichrysum cephaloideum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16132	Bryum argenteum	Species	Bryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18422	Stizolobium deeringianum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12860	Clione antarctica	Species	Clionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19086	Nematolepis phebalioides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19370	Coprosma areolata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19766	Viguiera linearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17894	Rhus vulgaris	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18041	Cladrastis platycarpa	Species	Fabaceae	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 NPC49362 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	25645
0.1-0.2	21341
0.2-0.3	1965
0.3-0.4	556
0.4-0.5	279
0.5-0.6	61
0.6-0.7	5
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
0.777	Intermediate Similarity	NPC475584
0.777	Intermediate Similarity	NPC475152
0.7183	Intermediate Similarity	NPC482012
0.7083	Intermediate Similarity	NPC482011
0.6988	Remote Similarity	NPC476113
0.6291	Remote Similarity	NPC482010
0.6111	Remote Similarity	NPC475394
0.6074	Remote Similarity	NPC475892
0.6038	Remote Similarity	NPC489208
0.5978	Remote Similarity	NPC475649
0.5943	Remote Similarity	NPC475527
0.5759	Remote Similarity	NPC489209
0.5687	Remote Similarity	NPC33012
0.5641	Remote Similarity	NPC309223
0.5625	Remote Similarity	NPC8524
0.5593	Remote Similarity	NPC475599
0.5556	Remote Similarity	NPC85154
0.55	Remote Similarity	NPC102505
0.55	Remote Similarity	NPC488514
0.5491	Remote Similarity	NPC23020
0.5385	Remote Similarity	NPC13998
0.5385	Remote Similarity	NPC475345
0.5369	Remote Similarity	NPC609281
0.5338	Remote Similarity	NPC481079
0.5337	Remote Similarity	NPC480422
0.5312	Remote Similarity	NPC70809
0.528	Remote Similarity	NPC220160
0.5276	Remote Similarity	NPC153673
0.5263	Remote Similarity	NPC607904
0.525	Remote Similarity	NPC144644
0.525	Remote Similarity	NPC170407
0.5235	Remote Similarity	NPC606145
0.5232	Remote Similarity	NPC606553
0.5227	Remote Similarity	NPC488619
0.5215	Remote Similarity	NPC68767
0.5197	Remote Similarity	NPC172365
0.5188	Remote Similarity	NPC481081
0.5185	Remote Similarity	NPC224381
0.5185	Remote Similarity	NPC142151
0.5183	Remote Similarity	NPC110385
0.5183	Remote Similarity	NPC51099
0.5181	Remote Similarity	NPC275225
0.5181	Remote Similarity	NPC480421
0.5169	Remote Similarity	NPC113620
0.5166	Remote Similarity	NPC207738
0.5161	Remote Similarity	NPC123199
0.5155	Remote Similarity	NPC302543
0.5155	Remote Similarity	NPC37860
0.513	Remote Similarity	NPC123522
0.5128	Remote Similarity	NPC283417
0.5128	Remote Similarity	NPC200049
0.5122	Remote Similarity	NPC293031
0.5114	Remote Similarity	NPC485563
0.5111	Remote Similarity	NPC100612
0.5092	Remote Similarity	NPC267694
0.5083	Remote Similarity	NPC488620
0.5082	Remote Similarity	NPC265699
0.5066	Remote Similarity	NPC104137
0.5066	Remote Similarity	NPC26626
0.5065	Remote Similarity	NPC610461
0.5064	Remote Similarity	NPC609305
0.5062	Remote Similarity	NPC470876
0.5062	Remote Similarity	NPC475514
0.5061	Remote Similarity	NPC250247
0.5058	Remote Similarity	NPC472268
0.5056	Remote Similarity	NPC472270
0.5056	Remote Similarity	NPC112492
0.5032	Remote Similarity	NPC79643
0.5028	Remote Similarity	NPC482013
0.5027	Remote Similarity	NPC174336

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC49362 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7326
0.1-0.2	1792
0.2-0.3	31
0.3-0.4	1
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