NPASS Compound

Natural Product: NPC253455

Natural Product ID	NPC253455
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OKVCTOBWIAGOMR-ACCUITESSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6440365
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

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 45 46 0 0 0 0 0 0 0 0999 V2000 4.8393 2.5804 -1.3508 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9474 1.8484 -0.8635 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6842 0.7239 -0.0981 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3741 0.3204 0.1872 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1033 -0.7930 0.9452 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7565 -1.2481 1.2657 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6464 -0.6538 0.8718 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3181 -1.1918 1.2484 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2169 -2.2257 1.9511 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9006 -0.4975 0.7876 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1048 -1.2400 1.3019 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4066 -0.6201 0.9003 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5719 -0.5601 -0.5932 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8879 0.0600 -0.9248 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0054 1.4171 -1.0948 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2219 2.0209 -1.4046 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3270 1.2065 -1.5390 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2366 -0.1589 -1.3735 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9986 -0.7267 -1.0633 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1895 -1.5009 1.4163 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4859 -1.1151 1.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7587 0.0010 0.3834 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0487 0.4184 0.0889 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1792 2.8363 -0.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3329 2.0089 -2.1511 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2497 3.5470 -1.7284 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5776 0.9106 -0.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6115 -2.1396 1.8721 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7325 0.2335 0.2688 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9226 0.5719 1.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9096 -0.4837 -0.3346 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0802 -1.2607 2.4155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0131 -2.2964 0.9778 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2317 -1.1766 1.3788 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4122 0.4191 1.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4866 -1.5650 -1.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7316 0.0529 -1.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1177 2.0219 -0.9815 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2666 3.0988 -1.5298 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2761 1.6972 -1.7828 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1298 -0.7413 -1.4903 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9524 -1.7831 -0.9401 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9856 -2.3915 2.0225 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3343 -1.6756 1.5164 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8190 0.0502 0.6295 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 6 7 2 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 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 5 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 22 3 1 0 19 14 1 0 1 24 1 0 1 25 1 0 1 26 1 0 4 27 1 0 6 28 1 0 7 29 1 0 10 30 1 0 10 31 1 0 11 32 1 0 11 33 1 0 12 34 1 0 12 35 1 0 13 36 1 0 13 37 1 0 15 38 1 0 16 39 1 0 17 40 1 0 18 41 1 0 19 42 1 0 20 43 1 0 21 44 1 0 23 45 1 0 M END

Standard InCHIKey	OKVCTOBWIAGOMR-ACCUITESSA-N
Standard InCHI	InChI=1S/C20H22O3/c1-23-20-15-17(12-14-19(20)22)11-13-18(21)10-6-5-9-16-7-3-2-4-8-16/h2-4,7-8,11-15,22H,5-6,9-10H2,1H3/b13-11+
SMILES	COc1cc(/C=C/C(=O)CCCCc2ccccc2)ccc1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	310.16	Volume:	342.642 ? Van der Waals volume.
Dense:	0.905	LogP:	3.903 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.41 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.747 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	14.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.581	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.964	Fsp³:	0.25
MCE-18:	11.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.977	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.057 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.93 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.617	Promiscuous compounds:	0.111

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.912	MDCK Permeability:	-4.456
Pgp-inhibitor:	0.994	Pgp-substrate:	0.02
PAMPA:	0.017 ? 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):	0.035
20% Bioavailability (F20%):	0.545	30% Bioavailability (F30%):	0.896
50% Bioavailability (F50%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.092
Plasma Protein Binding (PPB):	98.388%	Volume Distribution (VD):	-0.509
Fu:	0.931% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.881
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.173	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.074	CYP2C19-substrate:	0.684
CYP2C9-inhibitor:	0.047	CYP2C9-substrate:	0.786
CYP2D6-inhibitor:	0.951	CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.051	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.874 ? 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):

7.377

Half-life (T1/2):

0.608

ADMET: Toxicity

hERG Blockers:	0.758	hERG Blockers (10um):	0.839
Human Hepatotoxicity (H-HT):	0.628	Drug-induced Liver Injury (DILI):	0.096
AMES Toxicity:	0.236	Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.275	Skin Sensitization:	0.973
Carcinogencity:	0.068	Eye Corrosion:	0.702
Eye Irritation:	0.99	Respiratory Toxicity:	0.661
Drug-induced Neurotoxicity:	0.474	Ototoxicity:	0.167
Hematotoxicity:	0.093	Drug-induced Nephrotoxicity:	0.575
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.063
A549 Cytotoxicity:	0.559	Hek293 Cytotoxicity:	0.633
BCF:	1.678 ? 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:	4.534 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.709 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.303 ? 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
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(81)85171-0]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[11141121]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11514174]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	fruit	Hainan Island, China	1998	PMID[12398545]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO22375	Saussurea salicifolia	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18057725]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18293903]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19432411]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22277277]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO25106	Arnica parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23583435]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	PMID[24669201]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25757283]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO24456	Salvia lavandulifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36986494]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9157192]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO13455	Hemiselmis virescens	Species	Hemiselmidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24191	Drypetes tessmanniana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24754	Tsitsikamma favus	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18875	Aconitum contortum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24813	Agardhiella tenera	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24969	Ageratum mexicanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23660	Alpinia zerumbet	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25106	Arnica parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21799	Bacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22924	Bombus terrestris	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24118	Buxus hildebrandtii	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24937	Callicarpa acuminata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23149	Callistemon coccineus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24874	Croton geayi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24493	Echinacea simulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24659	Eremurus chinensis	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23750	Escontria chiotilla	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24021	Eucryphia cordifolia	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24589	Grindelia discoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18045	Holothuria atra	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25130	Hylotrupes bajulus	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23375	Hypericum reptans	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23288	Justicia betonica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25226	Kalanchoe spathulata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27093	Kniphofia foliosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21242	Neolitsea villosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21483	Nonomuraea dietziae	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20148	Nux prinsepiae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23657	Ophiocordyceps heteropoda	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25031	Petunia nyctaginiflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24268	Pteryxia terebinthina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24406	Rhizophora tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23837	Rubus laciniatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24456	Salvia lavandulifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22375	Saussurea salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27277	Stenocarpella maydis	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17445	Streptomyces corchorusii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24688	Streptomyces ramocissimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19716	Uvaria lucida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28259	Viguiera pinnatilobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25068	Zebrina pendula	Species	Enidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20148	Nux prinsepiae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23288	Justicia betonica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20148	Nux prinsepiae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23660	Alpinia zerumbet	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18045	Holothuria atra	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24937	Callicarpa acuminata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25130	Hylotrupes bajulus	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25106	Arnica parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24688	Streptomyces ramocissimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13455	Hemiselmis virescens	Species	Hemiselmidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23657	Ophiocordyceps heteropoda	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18875	Aconitum contortum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24969	Ageratum mexicanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23288	Justicia betonica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25031	Petunia nyctaginiflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25068	Zebrina pendula	Species	Enidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21242	Neolitsea villosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24191	Drypetes tessmanniana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27277	Stenocarpella maydis	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23149	Callistemon coccineus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24874	Croton geayi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23837	Rubus laciniatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21483	Nonomuraea dietziae	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24589	Grindelia discoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21799	Bacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22924	Bombus terrestris	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO23375	Hypericum reptans	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24493	Echinacea simulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24754	Tsitsikamma favus	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23750	Escontria chiotilla	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24659	Eremurus chinensis	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22375	Saussurea salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27093	Kniphofia foliosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25226	Kalanchoe spathulata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24268	Pteryxia terebinthina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24118	Buxus hildebrandtii	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24021	Eucryphia cordifolia	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17445	Streptomyces corchorusii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28259	Viguiera pinnatilobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24813	Agardhiella tenera	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24406	Rhizophora tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19716	Uvaria lucida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24456	Salvia lavandulifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2838	Verbena officinalis	Species	Verbenaceae	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	3
Inhibition	5

Activity Type	# Activity
Individual protein	1
Cell line	4
Organism	2
Unchecked	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	4000.0	nM	PMID[33422907]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell line	HUVEC	Homo sapiens	Inhibition	=	0.0	%	PMID[33422907]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	23000.0	nM	PMID[33422907]
NPT5272	Organism	Zingiber officinale	Zingiber officinale	IC50	=	2300.0	nM	PMID[33422907]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	52.0	%	PMID[33422907]

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 NPC253455 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Natural Product ID

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC253455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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