NPASS Compound

Natural Product: NPC121703

Natural Product ID	NPC121703
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oxytroflavoside D
IUPAC Name	(3S)-3-hydroxy-3-methyl-5-oxo-5-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxyoxan-2-yl]methoxy]pentanoic acid
Synonyms	Oxytroflavoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2071420
PubChem CID	60200221
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 73 76 0 0 0 0 0 0 0 0999 V2000 -6.8907 1.7259 -1.3838 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0433 0.2622 -1.1581 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7202 -0.1526 0.0964 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0826 0.3008 1.3463 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1302 1.5300 1.6455 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4459 -0.5716 2.1863 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7931 -0.4860 -1.4309 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6009 -0.1366 -0.6587 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6080 0.7641 0.1943 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3794 -0.7932 -0.8308 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2354 -0.4802 -0.0970 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0987 -1.3268 -0.5873 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4310 -2.7924 -0.6924 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1409 -3.5999 -0.6657 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9123 -2.7770 -1.3993 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1602 -1.4581 -0.7337 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1029 -1.1201 0.0840 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4129 -1.5011 -0.0791 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2685 -0.4112 -0.0591 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0509 -0.1933 -1.2076 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9760 -0.9639 -2.1957 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9018 0.8732 -1.2447 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7057 1.1728 -2.3249 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5646 2.2452 -2.3807 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5892 3.0620 -1.2392 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7923 2.7642 -0.1685 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9300 1.6761 -0.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1897 1.4339 0.9143 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3410 0.4062 1.0133 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5891 0.2735 2.2700 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8725 -0.8148 2.6629 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1962 -0.8443 3.8585 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1864 0.2063 4.7475 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9159 1.3222 4.3553 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5894 1.3426 3.1555 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5038 0.1705 5.9510 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4253 4.1770 -1.1970 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2736 4.5158 -2.2977 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6581 0.3361 -3.4462 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5104 -2.6294 -2.7349 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2222 -3.9296 0.6146 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2727 -3.1045 0.3722 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9189 -0.1685 -2.2596 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8747 1.9249 -2.4935 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7710 2.2829 -0.9801 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9456 2.1675 -1.0138 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7788 0.2355 0.0437 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8278 -1.2779 0.1534 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1261 -0.3618 3.1009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9912 -1.6123 -1.3815 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5938 -0.3636 -2.5518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9108 0.5851 -0.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3940 -0.6159 1.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9328 -0.9968 -1.6605 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0216 -2.9619 -1.6169 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3217 -4.5130 -1.2651 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8835 -3.3384 -1.4436 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2966 -0.6179 -1.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1946 2.4935 -3.2142 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8069 3.3938 0.7185 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8413 -1.6888 2.0468 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6380 -1.7312 4.1399 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9337 2.1680 5.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1609 2.2268 2.8573 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7971 -0.5649 6.6106 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8319 3.6005 -2.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6652 4.9209 -3.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9677 5.2942 -1.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3551 -0.4182 -3.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2652 -2.8025 -3.3541 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0645 -3.1459 1.2248 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1320 -3.4998 0.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1290 -1.0882 -1.9998 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 25 37 1 0 37 38 1 0 23 39 1 0 15 40 1 0 14 41 1 0 13 42 1 0 2 43 1 6 17 12 1 0 29 19 2 0 35 30 1 0 27 22 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 0 3 48 1 0 6 49 1 0 7 50 1 0 7 51 1 0 11 52 1 0 11 53 1 0 12 54 1 6 13 55 1 6 14 56 1 6 15 57 1 6 16 58 1 6 24 59 1 0 26 60 1 0 31 61 1 0 32 62 1 0 34 63 1 0 35 64 1 0 36 65 1 0 38 66 1 0 38 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	ZADGYZMBIIDGTO-QQLUSITOSA-N
Standard InCHI	InChI=1S/C28H30O15/c1-28(38,9-18(31)32)10-19(33)40-11-17-21(34)23(36)24(37)27(42-17)43-26-22(35)20-15(30)7-14(39-2)8-16(20)41-25(26)12-3-5-13(29)6-4-12/h3-8,17,21,23-24,27,29-30,34,36-38H,9-11H2,1-2H3,(H,31,32)/t17-,21+,23+,24-,27+,28+/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)OC)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	606.16	Volume:	564.107 ? Van der Waals volume.
Dense:	1.075	LogP:	1.382 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.642 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.996 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	26.0
TPSA:	242.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.153	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.367	Fsp³:	0.393
MCE-18:	100.949 ? 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:	0.418	Fluc inhibitor:	0.375 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.911 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.632 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.027	Promiscuous compounds:	0.436

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.019	MDCK Permeability:	-5.23
Pgp-inhibitor:	0.0	Pgp-substrate:	0.075
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):	0.272
20% Bioavailability (F20%):	0.888	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.2
Plasma Protein Binding (PPB):	89.231%	Volume Distribution (VD):	-0.136
Fu:	8.696% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.034
BSEP inhibitor:	0.023

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:	0.499
HLM stability:	0.019 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.315

Half-life (T1/2):

2.123

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.941	Drug-induced Liver Injury (DILI):	0.606
AMES Toxicity:	0.492	Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.394	Skin Sensitization:	1.0
Carcinogencity:	0.458	Eye Corrosion:	0.0
Eye Irritation:	0.902	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.666
Hematotoxicity:	0.306	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	0.99	RPMI-8226 Immunitoxicity:	0.094
A549 Cytotoxicity:	0.116	Hek293 Cytotoxicity:	0.328
BCF:	0.3 ? 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:	2.744 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.21 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.345 ? 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 NPC121703 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	8441
0.1-0.2	36705
0.2-0.3	3713
0.3-0.4	521
0.4-0.5	311
0.5-0.6	126
0.6-0.7	24
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	NPC277532
0.7941	Intermediate Similarity	NPC209550
0.6889	Remote Similarity	NPC46420
0.6804	Remote Similarity	NPC186816
0.6789	Remote Similarity	NPC138990
0.6735	Remote Similarity	NPC64051
0.6727	Remote Similarity	NPC175429
0.6667	Remote Similarity	NPC480445
0.6484	Remote Similarity	NPC249281
0.6413	Remote Similarity	NPC297987
0.64	Remote Similarity	NPC153755
0.6373	Remote Similarity	NPC486577
0.6364	Remote Similarity	NPC150164
0.6354	Remote Similarity	NPC276377
0.6275	Remote Similarity	NPC229409
0.6275	Remote Similarity	NPC72016
0.625	Remote Similarity	NPC116458
0.625	Remote Similarity	NPC246943
0.625	Remote Similarity	NPC480444
0.6238	Remote Similarity	NPC46202
0.617	Remote Similarity	NPC271692
0.6122	Remote Similarity	NPC116864
0.6122	Remote Similarity	NPC244776
0.6	Remote Similarity	NPC85751
0.6	Remote Similarity	NPC19240
0.6	Remote Similarity	NPC609888
0.598	Remote Similarity	NPC129264
0.5943	Remote Similarity	NPC36138
0.5941	Remote Similarity	NPC173582
0.5941	Remote Similarity	NPC265885
0.5941	Remote Similarity	NPC181465
0.5941	Remote Similarity	NPC215710
0.5941	Remote Similarity	NPC473438
0.5941	Remote Similarity	NPC253788
0.5922	Remote Similarity	NPC64425
0.5909	Remote Similarity	NPC217520
0.5905	Remote Similarity	NPC142142
0.5888	Remote Similarity	NPC470450
0.5842	Remote Similarity	NPC471079
0.5825	Remote Similarity	NPC473571
0.5825	Remote Similarity	NPC110941
0.581	Remote Similarity	NPC270448
0.5789	Remote Similarity	NPC289667
0.5766	Remote Similarity	NPC25523
0.5729	Remote Similarity	NPC158674
0.5729	Remote Similarity	NPC136042
0.5727	Remote Similarity	NPC470416
0.5714	Remote Similarity	NPC611303
0.5701	Remote Similarity	NPC476472
0.5701	Remote Similarity	NPC294815
0.5701	Remote Similarity	NPC470447
0.5701	Remote Similarity	NPC16194
0.5688	Remote Similarity	NPC214621
0.5688	Remote Similarity	NPC34267
0.567	Remote Similarity	NPC84362
0.5648	Remote Similarity	NPC470449
0.5619	Remote Similarity	NPC470125
0.5619	Remote Similarity	NPC240306
0.5607	Remote Similarity	NPC270675
0.5607	Remote Similarity	NPC195685
0.56	Remote Similarity	NPC605784
0.5596	Remote Similarity	NPC223426
0.5577	Remote Similarity	NPC65563
0.5577	Remote Similarity	NPC470949
0.5556	Remote Similarity	NPC80068
0.5545	Remote Similarity	NPC470455
0.5536	Remote Similarity	NPC480796
0.5536	Remote Similarity	NPC472993
0.5536	Remote Similarity	NPC477895
0.5526	Remote Similarity	NPC139571
0.5521	Remote Similarity	NPC111929
0.5521	Remote Similarity	NPC320283
0.5521	Remote Similarity	NPC41121
0.5514	Remote Similarity	NPC32641
0.5514	Remote Similarity	NPC256188
0.5514	Remote Similarity	NPC35119
0.551	Remote Similarity	NPC24043
0.549	Remote Similarity	NPC172807
0.5481	Remote Similarity	NPC44931
0.5464	Remote Similarity	NPC77672
0.5464	Remote Similarity	NPC133671
0.5464	Remote Similarity	NPC135391
0.5464	Remote Similarity	NPC78263
0.5464	Remote Similarity	NPC250069
0.5455	Remote Similarity	NPC472994
0.5446	Remote Similarity	NPC189564
0.5429	Remote Similarity	NPC203259
0.5429	Remote Similarity	NPC33054
0.5429	Remote Similarity	NPC176740
0.5429	Remote Similarity	NPC471725
0.5429	Remote Similarity	NPC134532
0.5429	Remote Similarity	NPC156869
0.5429	Remote Similarity	NPC602582
0.5424	Remote Similarity	NPC470720
0.5421	Remote Similarity	NPC470443
0.537	Remote Similarity	NPC37668
0.537	Remote Similarity	NPC473327
0.5354	Remote Similarity	NPC488080
0.5354	Remote Similarity	NPC169977
0.5351	Remote Similarity	NPC164704
0.5339	Remote Similarity	NPC470717
0.5333	Remote Similarity	NPC67326
0.5327	Remote Similarity	NPC296018
0.5327	Remote Similarity	NPC488073
0.5327	Remote Similarity	NPC126784
0.5327	Remote Similarity	NPC241423
0.5327	Remote Similarity	NPC488074
0.53	Remote Similarity	NPC472459
0.5294	Remote Similarity	NPC223747
0.5288	Remote Similarity	NPC251417
0.5278	Remote Similarity	NPC211532
0.5273	Remote Similarity	NPC471669
0.5268	Remote Similarity	NPC81042
0.5243	Remote Similarity	NPC203050
0.5243	Remote Similarity	NPC225434
0.5229	Remote Similarity	NPC606657
0.5225	Remote Similarity	NPC101636
0.5225	Remote Similarity	NPC298171
0.5225	Remote Similarity	NPC470445
0.5217	Remote Similarity	NPC480441
0.5192	Remote Similarity	NPC477848
0.5189	Remote Similarity	NPC67105
0.5179	Remote Similarity	NPC470446
0.5172	Remote Similarity	NPC146679
0.5167	Remote Similarity	NPC488079
0.5167	Remote Similarity	NPC488078
0.5155	Remote Similarity	NPC288084
0.5152	Remote Similarity	NPC108831
0.5152	Remote Similarity	NPC182634
0.5149	Remote Similarity	NPC27942
0.5143	Remote Similarity	NPC254540
0.514	Remote Similarity	NPC22062
0.514	Remote Similarity	NPC473634
0.514	Remote Similarity	NPC210073
0.514	Remote Similarity	NPC138811
0.5138	Remote Similarity	NPC65711
0.5135	Remote Similarity	NPC473073
0.5128	Remote Similarity	NPC470716
0.51	Remote Similarity	NPC64305
0.51	Remote Similarity	NPC323593
0.51	Remote Similarity	NPC203500
0.5098	Remote Similarity	NPC159579
0.5098	Remote Similarity	NPC175107
0.5091	Remote Similarity	NPC209296
0.5086	Remote Similarity	NPC470715
0.5052	Remote Similarity	NPC54802
0.5052	Remote Similarity	NPC197304
0.5051	Remote Similarity	NPC331652
0.505	Remote Similarity	NPC27640
0.5047	Remote Similarity	NPC39834
0.5045	Remote Similarity	NPC479766
0.5043	Remote Similarity	NPC470451

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC121703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2764
0.1-0.2	6249
0.2-0.3	128
0.3-0.4	3
0.4-0.5	2
0.5-0.6	3
0.6-0.7	1
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
0.6	Remote Similarity	NPD7251	Phase 2
0.5636	Remote Similarity	NPD7808	Phase 3
0.5429	Remote Similarity	NPD6797	Phase 2
0.5091	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