NPASS Compound

Natural Product: NPC165977

Natural Product ID	NPC165977
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Fuscaxanthone C
IUPAC Name	1-hydroxy-3,6,7-trimethoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
Synonyms	Di-O-Methylmangostin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL464524
PubChem CID	231412
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

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 62 64 0 0 0 0 0 0 0 0999 V2000 -5.7630 -0.3132 -1.1408 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9135 -0.7215 -0.0646 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6255 -1.1321 -0.3294 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3876 -2.4653 -0.5947 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4692 -3.3418 -0.5811 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3510 -4.7164 -0.8350 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1109 -2.9035 -0.8639 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0476 -1.9997 -0.8690 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3057 -0.6650 -0.6001 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5711 -0.2042 -0.3298 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8097 1.2119 -0.0251 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8568 1.5130 1.4059 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8418 2.0706 2.0254 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1072 2.5049 1.3757 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7533 2.3219 3.5225 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2563 0.2134 -0.6009 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3625 1.4509 -0.3659 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0329 -0.2575 -0.8736 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1775 -1.5963 -1.1288 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1640 -2.4284 -1.1235 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4719 -2.0436 -1.3987 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5283 -1.1604 -1.4009 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3780 0.1851 -1.1436 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1040 0.6391 -0.8757 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8618 1.9820 -0.6053 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5328 1.1306 -1.1477 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3129 0.9563 0.1067 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5240 1.8943 0.9907 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3249 1.6189 2.2250 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0049 3.2851 0.8585 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8416 -1.5785 -1.6685 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0394 -2.9708 -1.9409 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1606 -0.2760 -2.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6149 -1.0479 -1.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1663 0.7028 -0.9874 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3049 -5.1983 -0.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -5.1578 -0.2623 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2523 -4.9131 -1.9135 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9085 -3.9274 -1.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3849 1.9567 -0.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9392 1.3197 -0.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9552 1.2261 1.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6669 3.2212 2.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6980 1.5916 1.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8498 2.9595 0.3955 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7613 2.1439 3.9491 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9621 1.7332 3.9832 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5977 3.4336 3.6147 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6214 -3.0827 -1.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7855 2.2471 0.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1914 2.1694 -1.2910 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1353 0.8733 -2.0478 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7363 -0.0432 0.2873 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2355 2.2526 2.2511 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7157 1.8007 3.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6565 0.5621 2.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6473 4.0108 1.4313 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0104 3.3365 1.3649 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0028 3.6551 -0.1718 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0904 -3.2051 -2.1171 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4675 -3.2824 -2.8278 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6719 -3.5423 -1.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 4 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 3 13 14 1 0 13 15 1 0 9 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 23 26 1 0 26 27 1 0 27 28 2 3 28 29 1 0 28 30 1 0 22 31 1 0 31 32 1 0 10 3 1 0 24 18 1 0 20 8 1 0 1 33 1 0 1 34 1 0 1 35 1 0 6 36 1 0 6 37 1 0 6 38 1 0 7 39 1 0 11 40 1 0 11 41 1 0 12 42 1 0 14 43 1 0 14 44 1 0 14 45 1 0 15 46 1 0 15 47 1 0 15 48 1 0 21 49 1 0 25 50 1 0 26 51 1 0 26 52 1 0 27 53 1 0 29 54 1 0 29 55 1 0 29 56 1 0 30 57 1 0 30 58 1 0 30 59 1 0 32 60 1 0 32 61 1 0 32 62 1 0 M END

Standard InCHIKey	FCIKYGUVHWZSJV-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C26H30O6/c1-14(2)8-10-16-18(29-5)12-20-23(24(16)27)25(28)22-17(11-9-15(3)4)26(31-7)21(30-6)13-19(22)32-20/h8-9,12-13,27H,10-11H2,1-7H3
SMILES	COc1c(OC)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	438.2	Volume:	461.596 ? Van der Waals volume.
Dense:	0.949	LogP:	6.155 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.338 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.681 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	19.0
TPSA:	78.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.377	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.021	Fsp³:	0.346
MCE-18:	22.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.948	Fluc inhibitor:	0.285 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.932 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.854 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.248	Promiscuous compounds:	0.199

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.953	MDCK Permeability:	-4.638
Pgp-inhibitor:	0.999	Pgp-substrate:	0.042
PAMPA:	0.009 ? 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):	0.451
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.956
Plasma Protein Binding (PPB):	95.0%	Volume Distribution (VD):	0.284
Fu:	4.566% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.999
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.33	CYP2D6-substrate:	0.563
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

6.305

Half-life (T1/2):

0.914

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.513
Human Hepatotoxicity (H-HT):	0.489	Drug-induced Liver Injury (DILI):	0.794
AMES Toxicity:	0.623	Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.52	Skin Sensitization:	0.884
Carcinogencity:	0.703	Eye Corrosion:	0.001
Eye Irritation:	0.447	Respiratory Toxicity:	0.938
Drug-induced Neurotoxicity:	0.377	Ototoxicity:	0.376
Hematotoxicity:	0.31	Drug-induced Nephrotoxicity:	0.55
Genotoxicity:	0.824	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.252	Hek293 Cytotoxicity:	0.487
BCF:	2.376 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.95 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.661 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.083 ? 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
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11161	Cratoxylum arborescens	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11161	Cratoxylum arborescens	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11161	Cratoxylum arborescens	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9717	Wibelia divaricata	Species	Davalliaceae	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
IC50	2
Inhibition	13
ED50	1
MIC	13

Activity Type	# Activity
Cell line	2
Organism	25
Individual protein	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT721	Individual protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[21428375]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[21428375]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	1400.0	nM	PMID[21428375]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[25651042]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	7.0	%	PMID[9213587]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	9.0	%	PMID[9213587]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	27.0	%	PMID[9213587]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	41.0	%	PMID[9213587]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	5.0	%	PMID[9213587]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	12.0	%	PMID[9213587]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	16.0	%	PMID[9213587]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	17.0	%	PMID[9213587]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	128.0	ug.mL-1	PMID[25651042]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	75.0	ug.mL-1	PMID[32795625]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	14.0	%	PMID[9213587]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	22.0	%	PMID[9213587]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	16.0	%	PMID[9213587]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[25651042]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[25651042]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128.0	ug.mL-1	PMID[25651042]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	300.0	ug.mL-1	PMID[32795625]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	150.0	ug.mL-1	PMID[32795625]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	300.0	ug.mL-1	PMID[32795625]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	300.0	ug.mL-1	PMID[32795625]
NPT2	Others	Unspecified	n.a.	Inhibition	=	53.8	%	PMID[25651042]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	128.0	ug.mL-1	PMID[25651042]
NPT1242	Organism	Salmonella typhi	Salmonella enterica subsp. enterica serovar Typhi	MIC	=	300.0	ug.mL-1	PMID[32795625]
NPT1243	Organism	Shigella sonnei	Shigella sonnei	MIC	>	300.0	ug.mL-1	PMID[32795625]

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 NPC165977 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	22484
0.1-0.2	22349
0.2-0.3	4469
0.3-0.4	461
0.4-0.5	64
0.5-0.6	12
0.6-0.7	7
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC474186
0.8644	High Similarity	NPC475886
0.8361	Intermediate Similarity	NPC474350
0.8095	Intermediate Similarity	NPC474287
0.8095	Intermediate Similarity	NPC475883
0.8095	Intermediate Similarity	NPC474187
0.7846	Intermediate Similarity	NPC474351
0.7541	Intermediate Similarity	NPC14353
0.7541	Intermediate Similarity	NPC56085
0.7273	Intermediate Similarity	NPC229632
0.7258	Intermediate Similarity	NPC602307
0.6875	Remote Similarity	NPC604618
0.6462	Remote Similarity	NPC266499
0.6429	Remote Similarity	NPC152659
0.6129	Remote Similarity	NPC174999
0.6119	Remote Similarity	NPC152951
0.6111	Remote Similarity	NPC170245
0.6027	Remote Similarity	NPC239752
0.5972	Remote Similarity	NPC236521
0.589	Remote Similarity	NPC117854
0.5541	Remote Similarity	NPC472450
0.5541	Remote Similarity	NPC275780
0.5507	Remote Similarity	NPC228785
0.5352	Remote Similarity	NPC219917
0.5211	Remote Similarity	NPC482708
0.52	Remote Similarity	NPC326520
0.52	Remote Similarity	NPC310349
0.5143	Remote Similarity	NPC241904
0.5139	Remote Similarity	NPC217677
0.5135	Remote Similarity	NPC26051

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC165977 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3406
0.1-0.2	5619
0.2-0.3	124
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