NPASS Compound

Natural Product: NPC277532

Natural Product ID	NPC277532
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oxytroflavoside E
IUPAC Name	(3S)-3-hydroxy-3-methyl-5-oxo-5-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-7-methoxy-4-oxo-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-3-yl]oxyoxan-2-yl]methoxy]pentanoic acid
Synonyms	Oxytroflavoside E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2071421
PubChem CID	60200222
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 94 98 0 0 0 0 0 0 0 0999 V2000 6.5312 4.3958 1.7201 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0537 3.6798 0.4968 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2485 4.2150 -0.6962 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4597 5.6810 -0.8037 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2163 6.2538 0.0381 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8661 6.4545 -1.7849 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9109 2.1829 0.6054 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5045 1.7449 0.7690 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1013 1.6059 1.9704 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6198 1.4821 -0.2407 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2872 1.0611 -0.0859 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1913 -0.2820 0.6247 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8727 -1.3602 -0.1946 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9475 -2.5890 0.7200 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7649 -2.6278 1.6204 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5666 -1.9037 1.0467 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8569 -0.5997 0.7402 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9713 -2.5881 -0.0625 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0970 -3.4170 -0.0163 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1161 -4.7946 0.1556 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2562 -5.3086 0.2560 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9593 -5.6469 0.2179 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7722 -7.0029 0.3891 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8658 -7.8335 0.4497 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1380 -7.3371 0.3431 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3510 -6.0057 0.1741 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2565 -5.1595 0.1116 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4005 -3.8918 -0.0470 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3817 -3.0067 -0.1168 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7807 -1.6343 -0.2978 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0925 -1.2193 -0.0064 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5325 0.0652 -0.2214 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6945 1.0216 -0.7414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4037 0.6461 -1.0384 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9704 -0.6744 -0.8124 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0483 2.3278 -0.9874 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2633 2.9516 -0.7843 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2359 4.0466 0.2784 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6679 4.2633 0.7172 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4574 4.6652 -0.5262 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2176 3.6408 -1.5849 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0703 3.8008 -2.8008 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7494 4.9455 -3.5273 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8459 3.5328 -1.9059 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8042 4.5889 -0.1655 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6776 5.2836 1.6671 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4045 3.7476 1.3334 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2047 -8.2232 0.4112 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0559 -9.5978 0.5836 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5329 -7.4746 0.4940 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0519 -2.0183 2.8643 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1255 -3.7454 -0.0187 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0679 -1.6154 -1.3015 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3872 4.0219 0.2934 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3793 3.7041 2.5856 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3198 5.1126 2.0868 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6488 5.0262 1.5059 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5877 3.6919 -1.6133 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1550 4.0207 -0.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0786 7.4210 -1.9670 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5392 1.8622 1.4681 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3643 1.7339 -0.3044 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7785 1.8105 0.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8017 1.0475 -1.0801 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6524 -0.1727 1.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8993 -1.0525 -0.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8602 -2.4572 1.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4915 -3.6518 1.8640 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8097 -1.9281 1.8538 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6607 -8.8906 0.5845 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3252 -5.5509 0.0838 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7375 -1.9959 0.4053 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5534 0.3131 0.0260 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6898 1.3615 -1.4547 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0316 -0.8660 -1.1155 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9999 2.2097 -0.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9432 4.9835 -0.2656 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0317 3.2975 1.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1476 5.6823 -0.7690 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4674 2.6394 -1.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1275 3.8051 -2.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9004 2.9166 -3.4590 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2034 5.7468 -3.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2559 5.4645 -0.1530 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5615 5.7560 1.5700 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5971 4.3151 1.2431 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0648 -10.0061 0.8752 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3130 -9.7884 1.3683 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7511 -10.1042 -0.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9556 -7.4483 1.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2840 -1.4777 3.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9970 -4.5219 0.5663 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6401 -2.0304 -2.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9478 3.2723 0.6462 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 4 6 1 0 2 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 25 48 1 0 48 49 1 0 23 50 1 0 15 51 1 0 14 52 1 0 13 53 1 0 2 54 1 6 17 12 1 0 29 19 2 0 35 30 1 0 44 37 1 0 27 22 1 0 1 55 1 0 1 56 1 0 1 57 1 0 3 58 1 0 3 59 1 0 6 60 1 0 7 61 1 0 7 62 1 0 11 63 1 0 11 64 1 0 12 65 1 1 13 66 1 6 14 67 1 1 15 68 1 1 16 69 1 1 24 70 1 0 26 71 1 0 31 72 1 0 32 73 1 0 34 74 1 0 35 75 1 0 37 76 1 1 38 77 1 6 39 78 1 1 40 79 1 6 41 80 1 1 42 81 1 0 42 82 1 0 43 83 1 0 45 84 1 0 46 85 1 0 47 86 1 0 49 87 1 0 49 88 1 0 49 89 1 0 50 90 1 0 51 91 1 0 52 92 1 0 53 93 1 0 54 94 1 0 M END

Standard InCHIKey	YYHLAMZVDLNYIY-ZNNIGJCWSA-N
Standard InCHI	InChI=1S/C34H40O20/c1-34(47,9-20(37)38)10-21(39)49-12-19-24(41)27(44)29(46)33(53-19)54-31-25(42)22-16(36)7-15(48-2)8-17(22)51-30(31)13-3-5-14(6-4-13)50-32-28(45)26(43)23(40)18(11-35)52-32/h3-8,18-19,23-24,26-29,32-33,35-36,40-41,43-47H,9-12H2,1-2H3,(H,37,38)/t18-,19-,23-,24+,26+,27+,28-,29-,32-,33+,34+/m1/s1
SMILES	C[C@](CC(=O)O)(CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	768.21	Volume:	703.278 ? Van der Waals volume.
Dense:	1.092	LogP:	0.709 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.442 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.637 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	32.0
TPSA:	322.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.082	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.093	Fsp³:	0.5
MCE-18:	132.294 ? 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:	0.434	Fluc inhibitor:	0.355 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.815 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.643 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.032	Promiscuous compounds:	0.511

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.347	MDCK Permeability:	-5.28
Pgp-inhibitor:	0.0	Pgp-substrate:	0.085
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):	0.966
20% Bioavailability (F20%):	0.603	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.018
Plasma Protein Binding (PPB):	80.365%	Volume Distribution (VD):	-0.244
Fu:	17.826% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
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:	0.034
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):

1.278

Half-life (T1/2):

3.583

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.979	Drug-induced Liver Injury (DILI):	0.973
AMES Toxicity:	0.903	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.016	Skin Sensitization:	1.0
Carcinogencity:	0.191	Eye Corrosion:	0.0
Eye Irritation:	0.076	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.986
Hematotoxicity:	0.589	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.982	RPMI-8226 Immunitoxicity:	0.183
A549 Cytotoxicity:	0.179	Hek293 Cytotoxicity:	0.113
BCF:	0.324 ? 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:	2.871 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.191 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.474 ? 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
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1007/s11418-005-0009-z]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257536]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[22032651]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22032651]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30219526]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36599374]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2439	Diplopterygium glaucum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2670	Maytenus chuchuhuasha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3838	Chrysosporum ovalisporum	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO593	Wikstroemia viridiflora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9594	Lysimachia fordiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9737	Ampelocera edentula	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5086	Alternaria macrospora	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21472	Pterolobium hexapetalum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9998	Abies excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10038.1	Abies pinsapo var. marocana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9091	Orthosiphon spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9867	Ixeris debilis	Species	Asteraceae	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
Cell line	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
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	<	5.0	%	PMID[22775441]

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 NPC277532 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	10081
0.1-0.2	34922
0.2-0.3	3813
0.3-0.4	588
0.4-0.5	317
0.5-0.6	122
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8723	High Similarity	NPC121703
0.7156	Intermediate Similarity	NPC209550
0.6923	Remote Similarity	NPC289667
0.6404	Remote Similarity	NPC138990
0.6316	Remote Similarity	NPC297987
0.6311	Remote Similarity	NPC46202
0.6207	Remote Similarity	NPC175429
0.6162	Remote Similarity	NPC116458
0.6162	Remote Similarity	NPC246943
0.602	Remote Similarity	NPC472459
0.6	Remote Similarity	NPC64425
0.6	Remote Similarity	NPC480445
0.598	Remote Similarity	NPC251417
0.5979	Remote Similarity	NPC64305
0.5979	Remote Similarity	NPC136042
0.5918	Remote Similarity	NPC46420
0.5918	Remote Similarity	NPC84362
0.5905	Remote Similarity	NPC186816
0.5849	Remote Similarity	NPC64051
0.5842	Remote Similarity	NPC605784
0.5841	Remote Similarity	NPC25523
0.5833	Remote Similarity	NPC486577
0.5763	Remote Similarity	NPC480444
0.5741	Remote Similarity	NPC229409
0.5701	Remote Similarity	NPC153755
0.5676	Remote Similarity	NPC135358
0.5644	Remote Similarity	NPC611303
0.5641	Remote Similarity	NPC295625
0.5619	Remote Similarity	NPC609888
0.5603	Remote Similarity	NPC470716
0.56	Remote Similarity	NPC24043
0.56	Remote Similarity	NPC271692
0.5565	Remote Similarity	NPC480441
0.5565	Remote Similarity	NPC470715
0.5556	Remote Similarity	NPC249281
0.5514	Remote Similarity	NPC150164
0.55	Remote Similarity	NPC95090
0.55	Remote Similarity	NPC27408
0.55	Remote Similarity	NPC158674
0.55	Remote Similarity	NPC470720
0.55	Remote Similarity	NPC488079
0.55	Remote Similarity	NPC488078
0.5481	Remote Similarity	NPC276377
0.5455	Remote Similarity	NPC72016
0.5455	Remote Similarity	NPC35119
0.5437	Remote Similarity	NPC120099
0.5437	Remote Similarity	NPC486578
0.5431	Remote Similarity	NPC164704
0.5429	Remote Similarity	NPC116864
0.5429	Remote Similarity	NPC244776
0.5417	Remote Similarity	NPC470717
0.5413	Remote Similarity	NPC488073
0.5413	Remote Similarity	NPC240306
0.54	Remote Similarity	NPC77672
0.54	Remote Similarity	NPC133671
0.54	Remote Similarity	NPC135391
0.54	Remote Similarity	NPC78263
0.54	Remote Similarity	NPC250069
0.537	Remote Similarity	NPC156869
0.5351	Remote Similarity	NPC14187
0.534	Remote Similarity	NPC488071
0.5333	Remote Similarity	NPC203050
0.5333	Remote Similarity	NPC488072
0.5333	Remote Similarity	NPC225434
0.5315	Remote Similarity	NPC32641
0.5315	Remote Similarity	NPC256188
0.5294	Remote Similarity	NPC488080
0.5294	Remote Similarity	NPC169977
0.5288	Remote Similarity	NPC22832
0.5288	Remote Similarity	NPC21666
0.5268	Remote Similarity	NPC142142
0.5268	Remote Similarity	NPC5319
0.5259	Remote Similarity	NPC189564
0.5243	Remote Similarity	NPC325555
0.5243	Remote Similarity	NPC226304
0.5238	Remote Similarity	NPC607707
0.5229	Remote Similarity	NPC22062
0.5229	Remote Similarity	NPC473634
0.5229	Remote Similarity	NPC138811
0.5221	Remote Similarity	NPC85751
0.5221	Remote Similarity	NPC76831
0.5221	Remote Similarity	NPC19240
0.5192	Remote Similarity	NPC60735
0.5192	Remote Similarity	NPC26230
0.5192	Remote Similarity	NPC285197
0.5189	Remote Similarity	NPC601586
0.5182	Remote Similarity	NPC129264
0.5179	Remote Similarity	NPC473327
0.5179	Remote Similarity	NPC606657
0.5175	Remote Similarity	NPC36138
0.5169	Remote Similarity	NPC217520
0.5164	Remote Similarity	NPC470719
0.5146	Remote Similarity	NPC73511
0.5143	Remote Similarity	NPC101026
0.5143	Remote Similarity	NPC148710
0.5143	Remote Similarity	NPC243930
0.5143	Remote Similarity	NPC488077
0.5143	Remote Similarity	NPC609478
0.514	Remote Similarity	NPC211594
0.5138	Remote Similarity	NPC173582
0.5138	Remote Similarity	NPC265885
0.5138	Remote Similarity	NPC181465
0.5138	Remote Similarity	NPC215710
0.5138	Remote Similarity	NPC275454
0.5138	Remote Similarity	NPC473438
0.5138	Remote Similarity	NPC253788
0.5133	Remote Similarity	NPC479766
0.513	Remote Similarity	NPC470450
0.5096	Remote Similarity	NPC42773
0.5096	Remote Similarity	NPC45522
0.5094	Remote Similarity	NPC311830
0.5088	Remote Similarity	NPC476472
0.5088	Remote Similarity	NPC294815
0.5088	Remote Similarity	NPC470447
0.5088	Remote Similarity	NPC479765
0.5088	Remote Similarity	NPC16194
0.5085	Remote Similarity	NPC477895
0.5049	Remote Similarity	NPC145038
0.5049	Remote Similarity	NPC56077
0.5049	Remote Similarity	NPC281131
0.5049	Remote Similarity	NPC253662
0.5049	Remote Similarity	NPC179950
0.5049	Remote Similarity	NPC277205
0.5049	Remote Similarity	NPC37919
0.5049	Remote Similarity	NPC323593
0.5049	Remote Similarity	NPC88789
0.5049	Remote Similarity	NPC203500
0.5049	Remote Similarity	NPC491374
0.5046	Remote Similarity	NPC471079
0.5045	Remote Similarity	NPC473571
0.5045	Remote Similarity	NPC110941
0.5044	Remote Similarity	NPC473623
0.5044	Remote Similarity	NPC270448
0.5044	Remote Similarity	NPC209296

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC277532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3133
0.1-0.2	5895
0.2-0.3	112
0.3-0.4	3
0.4-0.5	3
0.5-0.6	4
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
0.5575	Remote Similarity	NPD7808	Phase 3
0.5495	Remote Similarity	NPD7251	Phase 2
0.5268	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5044	Remote Similarity	NPD7054	Phase 4

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