NPASS Compound

Natural Product: NPC85715

Natural Product ID	NPC85715
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RTATXGUCZHCSNG-XMYBZUOWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 72 76 0 0 0 0 0 0 0 0999 V2000 -6.8857 0.9698 -0.4478 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7476 0.2808 0.2480 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1858 -0.4277 1.5189 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8980 -0.8878 2.2053 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2323 -1.8573 1.2523 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9658 -1.0820 -0.0425 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0568 -0.0510 0.1869 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8867 -0.3191 -0.5435 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8571 0.7755 -0.3307 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4061 2.1148 -0.6939 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3130 3.1543 -0.7617 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8001 2.5749 -1.6476 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2704 1.3380 -0.9157 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2610 0.4011 -1.1052 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5272 0.8600 -1.3522 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5184 0.4366 -0.5175 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3240 1.4417 0.0353 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1312 2.6334 -0.2414 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3321 1.0868 0.8894 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1789 2.0090 1.4866 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1808 1.6410 2.3395 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3496 0.2992 2.6116 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5108 -0.6148 2.0200 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4941 -0.2731 1.1575 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7154 -1.1705 0.6129 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7180 -0.8662 -0.2304 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9653 -1.9934 -0.7410 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1293 -1.9847 -1.8217 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4055 -3.0917 -2.2270 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4856 -4.2881 -1.5566 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3256 -4.3132 -0.4652 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0409 -3.2267 -0.0601 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7603 -5.4124 -1.9556 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3723 -0.0510 3.4798 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9913 3.3547 1.1988 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7579 3.5063 -1.9136 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7583 4.3625 -1.2307 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2863 2.5001 0.3169 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1402 -0.6349 -0.6110 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1403 -2.8574 0.9403 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1140 0.2448 2.4230 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9172 -1.5765 1.2457 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7855 0.8758 0.2125 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6313 2.0632 -0.5380 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1413 0.5350 -1.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9610 1.0118 0.5552 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7626 0.2610 2.1452 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1299 -1.4216 3.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2849 -2.2301 1.6462 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5248 -1.8447 -0.7432 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1715 -0.4092 -1.6078 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5099 -1.2862 -0.1987 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5124 0.7865 0.7219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9541 2.0281 -1.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1137 3.2468 0.2572 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3406 2.2918 -2.6342 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2724 1.5233 0.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8118 2.4029 2.7770 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6581 -1.6578 2.2447 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0642 -1.0513 -2.3986 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7663 -2.9908 -3.0963 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3862 -5.2719 0.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7016 -3.2927 0.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2463 -5.9644 -1.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3019 -0.2961 3.1841 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4170 3.6763 0.3231 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8757 4.1460 -1.1477 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7200 4.4847 -1.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4311 3.4682 0.3543 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9478 -3.2994 0.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6712 0.8941 2.9143 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5711 -1.6849 1.9801 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 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 22 34 1 0 20 35 1 0 12 36 1 0 11 37 1 0 10 38 1 0 6 39 1 0 5 40 1 0 4 41 1 0 3 42 1 0 39 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 24 19 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 1 3 47 1 1 4 48 1 1 5 49 1 1 6 50 1 6 8 51 1 0 8 52 1 0 9 53 1 1 10 54 1 6 11 55 1 1 12 56 1 6 13 57 1 1 21 58 1 0 23 59 1 0 28 60 1 0 29 61 1 0 31 62 1 0 32 63 1 0 33 64 1 0 34 65 1 0 35 66 1 0 36 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	RTATXGUCZHCSNG-XMYBZUOWSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17+,18+,20-,21-,22+,23+,26+,27-/m0/s1
SMILES	C[C@H]1[C@H]([C@@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(cc2)O)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	1.011 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.509 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.544 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.68	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0.608	Fluc inhibitor:	0.293 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.786 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.61 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.131	Promiscuous compounds:	0.531

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.564	MDCK Permeability:	-5.015
Pgp-inhibitor:	0.0	Pgp-substrate:	0.95
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):	0.234
20% Bioavailability (F20%):	0.22	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.015
Plasma Protein Binding (PPB):	85.171%	Volume Distribution (VD):	-0.0
Fu:	13.831% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.849
BSEP inhibitor:	0.068

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:	0.056
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.035
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.607 ? 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):

1.129

Half-life (T1/2):

3.911

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.212
Human Hepatotoxicity (H-HT):	0.528	Drug-induced Liver Injury (DILI):	0.921
AMES Toxicity:	0.767	Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.162	Skin Sensitization:	0.99
Carcinogencity:	0.076	Eye Corrosion:	0.0
Eye Irritation:	0.938	Respiratory Toxicity:	0.048
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.715
Hematotoxicity:	0.043	Drug-induced Nephrotoxicity:	0.269
Genotoxicity:	0.93	RPMI-8226 Immunitoxicity:	0.156
A549 Cytotoxicity:	0.717	Hek293 Cytotoxicity:	0.72
BCF:	0.726 ? 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:	3.367 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.588 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.941 ? 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
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO20288	Polytolypa hystricis	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8691217]
NPO21101	Felicia amelloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11064	Haemanthus toxicarius	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20015	Echinocystis lobata	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22599	Crataegus pontica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28627.1	Coptis trifolia subsp. groenlandica	Subspecies	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18684	Calophyllum thwaitesii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22529	Calceolaria thyrsiflora	Species	Calceolariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21822	Berberis crataegina	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16711	Baccharis solieri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22711	Athanasia dregeana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22871	Aster alpinus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21530	Arnica viscosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22812	Acacia cambagei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22294	Pteris inaequalis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22927	Xanthoparmelia pokornyi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21368	Tricholoma batschii	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19139	Senecio polyodon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23025	Roccellaria mollis	Species	Roccellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20592	Rhodoglossum japonicum	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23353	[polyangium] brachysporum	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20288	Polytolypa hystricis	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8198	Podocarpus montanus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23952	Phlomoides medicinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21951	Paramignya griffithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28078	Melaleuca decora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22650	Helenium quadridentatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8198	Podocarpus montanus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19139	Senecio polyodon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8198	Podocarpus montanus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19139	Senecio polyodon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22294	Pteris inaequalis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8198	Podocarpus montanus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22812	Acacia cambagei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22927	Xanthoparmelia pokornyi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23025	Roccellaria mollis	Species	Roccellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28627.1	Coptis trifolia subsp. groenlandica	Subspecies	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21530	Arnica viscosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22711	Athanasia dregeana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20288	Polytolypa hystricis	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28078	Melaleuca decora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20592	Rhodoglossum japonicum	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22871	Aster alpinus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21951	Paramignya griffithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16711	Baccharis solieri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19139	Senecio polyodon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22599	Crataegus pontica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23952	Phlomoides medicinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21368	Tricholoma batschii	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23353	[polyangium] brachysporum	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22529	Calceolaria thyrsiflora	Species	Calceolariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20015	Echinocystis lobata	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22294	Pteris inaequalis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22650	Helenium quadridentatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21822	Berberis crataegina	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8198	Podocarpus montanus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18684	Calophyllum thwaitesii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11064	Haemanthus toxicarius	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21101	Felicia amelloides	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

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 NPC85715 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	18805
0.1-0.2	27019
0.2-0.3	3009
0.3-0.4	511
0.4-0.5	220
0.5-0.6	42
0.6-0.7	95
0.7-0.8	0
0.8-0.85	16
0.85-0.9	2
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC173582
1.0	High Similarity	NPC265885
1.0	High Similarity	NPC181465
1.0	High Similarity	NPC215710
1.0	High Similarity	NPC473438
1.0	High Similarity	NPC253788
0.9114	High Similarity	NPC203259
0.9114	High Similarity	NPC33054
0.9114	High Similarity	NPC176740
0.9114	High Similarity	NPC471725
0.9114	High Similarity	NPC134532
0.9114	High Similarity	NPC602582
0.8625	High Similarity	NPC471079
0.8519	High Similarity	NPC39834
0.8471	Intermediate Similarity	NPC476472
0.8471	Intermediate Similarity	NPC294815
0.8471	Intermediate Similarity	NPC16194
0.8235	Intermediate Similarity	NPC473327
0.8193	Intermediate Similarity	NPC65563
0.8193	Intermediate Similarity	NPC470949
0.8158	Intermediate Similarity	NPC111929
0.8158	Intermediate Similarity	NPC320283
0.8158	Intermediate Similarity	NPC41121
0.8118	Intermediate Similarity	NPC12013
0.8118	Intermediate Similarity	NPC11432
0.8118	Intermediate Similarity	NPC477613
0.8095	Intermediate Similarity	NPC473571
0.8095	Intermediate Similarity	NPC110941
0.8095	Intermediate Similarity	NPC186816
0.8	Intermediate Similarity	NPC189564
0.7976	Intermediate Similarity	NPC156869
0.7889	Intermediate Similarity	NPC203145
0.7857	Intermediate Similarity	NPC67326
0.7753	Intermediate Similarity	NPC221342
0.7753	Intermediate Similarity	NPC476470
0.7667	Intermediate Similarity	NPC602448
0.75	Intermediate Similarity	NPC116864
0.75	Intermediate Similarity	NPC244776
0.7416	Intermediate Similarity	NPC122467
0.7386	Intermediate Similarity	NPC126784
0.7386	Intermediate Similarity	NPC241423
0.7375	Intermediate Similarity	NPC127546
0.7375	Intermediate Similarity	NPC57625
0.7375	Intermediate Similarity	NPC173637
0.7375	Intermediate Similarity	NPC317489
0.7375	Intermediate Similarity	NPC223424
0.7375	Intermediate Similarity	NPC600591
0.734	Intermediate Similarity	NPC292019
0.734	Intermediate Similarity	NPC202908
0.7273	Intermediate Similarity	NPC129264
0.7253	Intermediate Similarity	NPC89127
0.7191	Intermediate Similarity	NPC470125
0.7176	Intermediate Similarity	NPC476215
0.716	Intermediate Similarity	NPC77672
0.716	Intermediate Similarity	NPC133671
0.716	Intermediate Similarity	NPC135391
0.716	Intermediate Similarity	NPC78263
0.716	Intermediate Similarity	NPC250069
0.7126	Intermediate Similarity	NPC187379
0.7065	Intermediate Similarity	NPC85751
0.7065	Intermediate Similarity	NPC19240
0.7033	Intermediate Similarity	NPC270448
0.7	Intermediate Similarity	NPC153755
0.6947	Remote Similarity	NPC89052
0.6923	Remote Similarity	NPC470443
0.6875	Remote Similarity	NPC54802
0.6875	Remote Similarity	NPC197304
0.686	Remote Similarity	NPC223747
0.6854	Remote Similarity	NPC163242
0.6854	Remote Similarity	NPC272068
0.6842	Remote Similarity	NPC214621
0.6842	Remote Similarity	NPC34267
0.6832	Remote Similarity	NPC474522
0.6829	Remote Similarity	NPC135599
0.6829	Remote Similarity	NPC73855
0.6829	Remote Similarity	NPC113968
0.6829	Remote Similarity	NPC328940
0.6829	Remote Similarity	NPC277174
0.6829	Remote Similarity	NPC606877
0.6809	Remote Similarity	NPC292929
0.6804	Remote Similarity	NPC173837
0.679	Remote Similarity	NPC288084
0.6778	Remote Similarity	NPC605592
0.6742	Remote Similarity	NPC139320
0.6742	Remote Similarity	NPC609888
0.6735	Remote Similarity	NPC303694
0.6702	Remote Similarity	NPC473073
0.6702	Remote Similarity	NPC471669
0.6699	Remote Similarity	NPC241781
0.6667	Remote Similarity	NPC265530
0.6635	Remote Similarity	NPC192539
0.6632	Remote Similarity	NPC470449
0.6628	Remote Similarity	NPC159579
0.6628	Remote Similarity	NPC219904
0.6596	Remote Similarity	NPC142142
0.6588	Remote Similarity	NPC46420
0.6569	Remote Similarity	NPC480445
0.6566	Remote Similarity	NPC25523
0.6562	Remote Similarity	NPC223426
0.6548	Remote Similarity	NPC249281
0.6526	Remote Similarity	NPC470447
0.6517	Remote Similarity	NPC95866
0.6505	Remote Similarity	NPC156785
0.6505	Remote Similarity	NPC162394
0.6489	Remote Similarity	NPC37668
0.6484	Remote Similarity	NPC44931
0.6481	Remote Similarity	NPC473554
0.6471	Remote Similarity	NPC145038
0.6471	Remote Similarity	NPC56077
0.6471	Remote Similarity	NPC281131
0.6471	Remote Similarity	NPC253662
0.6471	Remote Similarity	NPC179950
0.6471	Remote Similarity	NPC88789
0.6471	Remote Similarity	NPC491374
0.6452	Remote Similarity	NPC296018
0.6452	Remote Similarity	NPC488073
0.6452	Remote Similarity	NPC488074
0.6437	Remote Similarity	NPC175107
0.6404	Remote Similarity	NPC276377
0.6327	Remote Similarity	NPC81042
0.6322	Remote Similarity	NPC216496
0.6311	Remote Similarity	NPC488734
0.6311	Remote Similarity	NPC488735
0.6311	Remote Similarity	NPC488739
0.6311	Remote Similarity	NPC488732
0.6311	Remote Similarity	NPC488738
0.6304	Remote Similarity	NPC470405
0.6304	Remote Similarity	NPC67105
0.6279	Remote Similarity	NPC64305
0.625	Remote Similarity	NPC129217
0.6238	Remote Similarity	NPC217520
0.6237	Remote Similarity	NPC155877
0.6237	Remote Similarity	NPC304741
0.6222	Remote Similarity	NPC170052
0.6222	Remote Similarity	NPC135846
0.619	Remote Similarity	NPC276222
0.619	Remote Similarity	NPC274618
0.619	Remote Similarity	NPC118284
0.619	Remote Similarity	NPC608147
0.6162	Remote Similarity	NPC470455
0.6139	Remote Similarity	NPC477895
0.6136	Remote Similarity	NPC472459
0.6132	Remote Similarity	NPC480444
0.6129	Remote Similarity	NPC471748
0.6118	Remote Similarity	NPC67037
0.6118	Remote Similarity	NPC255615
0.6111	Remote Similarity	NPC116458
0.6111	Remote Similarity	NPC246943
0.6075	Remote Similarity	NPC488737
0.6064	Remote Similarity	NPC210073
0.6064	Remote Similarity	NPC150164
0.6061	Remote Similarity	NPC470446
0.6044	Remote Similarity	NPC203050
0.6044	Remote Similarity	NPC225434
0.6036	Remote Similarity	NPC483159
0.6036	Remote Similarity	NPC483160
0.6022	Remote Similarity	NPC29958
0.6	Remote Similarity	NPC85707
0.5977	Remote Similarity	NPC19388
0.5977	Remote Similarity	NPC240431
0.5977	Remote Similarity	NPC55786
0.5962	Remote Similarity	NPC139571
0.596	Remote Similarity	NPC470445
0.5946	Remote Similarity	NPC487499
0.5941	Remote Similarity	NPC121703
0.5938	Remote Similarity	NPC154741
0.5922	Remote Similarity	NPC480441
0.5893	Remote Similarity	NPC275977
0.5893	Remote Similarity	NPC231787
0.5889	Remote Similarity	NPC60735
0.5889	Remote Similarity	NPC26230
0.5889	Remote Similarity	NPC48093
0.5888	Remote Similarity	NPC488740
0.5888	Remote Similarity	NPC488736
0.5888	Remote Similarity	NPC488733
0.5877	Remote Similarity	NPC487502
0.587	Remote Similarity	NPC66087
0.5859	Remote Similarity	NPC76831
0.5859	Remote Similarity	NPC220173
0.5843	Remote Similarity	NPC305811
0.5843	Remote Similarity	NPC271692
0.5824	Remote Similarity	NPC120099
0.5824	Remote Similarity	NPC224530
0.5816	Remote Similarity	NPC32641
0.5816	Remote Similarity	NPC256188
0.5816	Remote Similarity	NPC104883
0.5816	Remote Similarity	NPC72016
0.5816	Remote Similarity	NPC488679
0.58	Remote Similarity	NPC287889
0.58	Remote Similarity	NPC36138
0.5789	Remote Similarity	NPC72554
0.5789	Remote Similarity	NPC227508
0.5778	Remote Similarity	NPC325555
0.5778	Remote Similarity	NPC226304
0.5743	Remote Similarity	NPC470450
0.573	Remote Similarity	NPC297987
0.5729	Remote Similarity	NPC303913
0.5673	Remote Similarity	NPC219043
0.567	Remote Similarity	NPC255157
0.567	Remote Similarity	NPC259896

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC85715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5311
0.1-0.2	3783
0.2-0.3	43
0.3-0.4	7
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9114	High Similarity	NPD6797	Phase 2
0.6882	Remote Similarity	NPD7251	Phase 2
0.6263	Remote Similarity	NPD7808	Phase 3
0.55	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