NPASS Compound

Natural Product: NPC151923

Natural Product ID	NPC151923
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2E,5R)-2-Hexa-2,4-Diynylidene-1,6-Dioxaspiro[4.4]Nona-3,7-Diene
IUPAC Name	(2E,5R)-2-hexa-2,4-diynylidene-1,6-dioxaspiro[4.4]nona-3,7-diene
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL507354
PubChem CID	44575221
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

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 25 26 0 0 0 0 0 0 0 0999 V2000 5.6610 -2.4843 2.5445 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4396 -1.7014 2.3989 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3939 -1.0518 2.2768 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2135 -0.3340 2.1207 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1486 0.2920 1.9929 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0820 1.0086 1.8216 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7469 0.9799 0.6746 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2584 0.2180 -0.4747 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0930 0.3510 -1.4801 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1937 1.2367 -0.9983 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9421 1.5934 0.3093 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4617 0.3762 -1.1655 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6724 0.5485 -2.6165 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0830 1.6666 -2.9911 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4735 2.2780 -1.8754 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4072 -3.5535 2.7289 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3062 -2.1028 3.3448 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1555 -2.4630 1.5350 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5101 1.5968 2.6289 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6615 -0.3835 -0.5224 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0730 -0.0563 -2.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2541 0.8089 -0.5688 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2274 -0.6853 -0.8952 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2187 -0.1549 -3.2211 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0971 2.0163 -4.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 3 0 3 4 1 0 4 5 3 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 11 7 1 0 15 10 1 0 1 16 1 0 1 17 1 0 1 18 1 0 6 19 1 0 8 20 1 0 9 21 1 0 12 22 1 0 12 23 1 0 13 24 1 0 14 25 1 0 M END

Standard InCHIKey	IBELVOGDVQQPMZ-BWODNOAJSA-N
Standard InCHI	InChI=1S/C13H10O2/c1-2-3-4-5-7-12-8-10-13(15-12)9-6-11-14-13/h6-8,10-11H,9H2,1H3/b12-7+/t13-/m1/s1
SMILES	CC#CC#C/C=C/1C=C[C@]2(O1)CC=CO2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	198.07	Volume:	215.417 ? Van der Waals volume.
Dense:	0.919	LogP:	2.902 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.768 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.298 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	13.0
TPSA:	18.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	2.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.555	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.436	Fsp³:	0.231
MCE-18:	32.5 ? 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:	Rejected
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.01	Fluc inhibitor:	0.035 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.267 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.284 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.996	Promiscuous compounds:	0.097

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.35	MDCK Permeability:	-4.669
Pgp-inhibitor:	0.547	Pgp-substrate:	0.001
PAMPA:	0.976 ? 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):	0.155
20% Bioavailability (F20%):	0.121	30% Bioavailability (F30%):	0.116
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	93.789%	Volume Distribution (VD):	-0.05
Fu:	7.083% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.075
OATP1B3 inhibitor:	0.21	BCRP inhibitor:	0.994
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.249	CYP1A2-substrate:	0.502
CYP2C19-inhibitor:	0.176	CYP2C19-substrate:	0.481
CYP2C9-inhibitor:	0.751	CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.775	CYP2D6-substrate:	0.583
CYP3A4-inhibitor:	0.03	CYP3A4-substrate:	0.045
CYP2B6-substrate:	0.841	CYP2C8-inhibitor:	0.947
HLM stability:	0.312 ? 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):

5.94

Half-life (T1/2):

1.918

ADMET: Toxicity

hERG Blockers:	0.053	hERG Blockers (10um):	0.372
Human Hepatotoxicity (H-HT):	0.674	Drug-induced Liver Injury (DILI):	0.952
AMES Toxicity:	0.399	Rat Oral Acute Toxicity:	0.506
Maximum Recommended Daily Dose:	0.673	Skin Sensitization:	0.868
Carcinogencity:	0.862	Eye Corrosion:	0.954
Eye Irritation:	0.997	Respiratory Toxicity:	0.917
Drug-induced Neurotoxicity:	0.42	Ototoxicity:	0.191
Hematotoxicity:	0.049	Drug-induced Nephrotoxicity:	0.48
Genotoxicity:	0.46	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.022	Hek293 Cytotoxicity:	0.374
BCF:	1.366 ? 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:	3.983 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.523 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.953 ? 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
NPO2768	Berchemia floribunda	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200690067]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ja00388a092]
NPO11702	Plexaurella grisea	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325216]
NPO17377	Pittosporum viridiflorum	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809069]
NPO15579	Mycale laxissima	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932129]
NPO3028	Plagius flosculosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499337]
NPO16634	Sinularia manaarensis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933863]
NPO7664	Pseudocedrela kotschyi	Species	Meliaceae	Eukaryota	roots	n.a.	n.a.	PMID[17253841]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18640035]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193043]
NPO5018	Nervilia fordii	Species	Orchidaceae	Eukaryota	whole plant	n.a.	n.a.	PMID[19422205]
NPO11629	Brassica nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21861458]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25932671]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	Gulf of Aomori, Japan	n.a.	PMID[8691208]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8699184]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882431]
NPO16120	Swertia decora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO2768	Berchemia floribunda	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO752	Oligonychus bessardi	Species	Tetranychidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16789	Erythrina sandwicensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16878	Roldana barba-johannis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17447	Agathosma betulina	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9964	Aglaia lawii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12087	Amaioua guianensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8782	Arnica sachalinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16466	Baccharis santelicis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3742	Betula maximowicziana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22541	Channa argus	Species	Channidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16713	Choisya arizonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15904	Chrysosplenium oppositifolium	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13773	Eriogonum nudum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15194	Euphorbia balsamifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6899	Hepialus hecta	Species	Hepialidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22394	Hyacinthoides hispanica	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5824	Hygrophila polysperma	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11413	Incarvillea emodi	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13410	Mcneillia graminifolia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15341	Mucuna sloanei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15579	Mycale laxissima	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1354	Myelochroa rhytidodes	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5018	Nervilia fordii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13130	Notholaena peninsularis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16313	Ochrocarpos odoratus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13296	Pinus sitchensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17377	Pittosporum viridiflorum	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11702	Plexaurella grisea	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7664	Pseudocedrela kotschyi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27425	Pseudotaxus chienii	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9425	Punctelia microsticta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21773	Rothmannia urcelliformis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14625	Santolina rosmarinifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15691	Senecio coahuilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15452	Senecio othonniformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16223	Serratula xeranthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16634	Sinularia manaarensis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8298	Sphaeria biglobosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1780	Sphaeria doliolum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16120	Swertia decora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16553	Theonella cupola	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29072	Tritomaria quinquedentata	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27420	Venidium hirsutum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14127	Veratrum eschscholtzii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26942	Vicoa vestita	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11629	Brassica nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3028	Plagius flosculosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18469	Anochetus mayri	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19109	Cetraria sanguinea	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18201	Gonimbrasia belina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19655	Larix sukaczewii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18798	Parmelia perlata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15940	Pinus gerardiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19200	Rolandra fruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18546	Senna longiracemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15577	Volvariella volvacea	Species	Pluteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11629	Brassica nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22541	Channa argus	Species	Channidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9964	Aglaia lawii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15904	Chrysosplenium oppositifolium	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11629	Brassica nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14127	Veratrum eschscholtzii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15577	Volvariella volvacea	Species	Pluteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14625	Santolina rosmarinifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16466	Baccharis santelicis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15579	Mycale laxissima	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11413	Incarvillea emodi	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5018	Nervilia fordii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13296	Pinus sitchensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7664	Pseudocedrela kotschyi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12087	Amaioua guianensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16120	Swertia decora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5824	Hygrophila polysperma	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15691	Senecio coahuilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16878	Roldana barba-johannis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13130	Notholaena peninsularis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15940	Pinus gerardiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16789	Erythrina sandwicensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9964	Aglaia lawii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14127	Veratrum eschscholtzii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11702	Plexaurella grisea	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16634	Sinularia manaarensis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO752	Oligonychus bessardi	Species	Tetranychidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21773	Rothmannia urcelliformis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17377	Pittosporum viridiflorum	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8298	Sphaeria biglobosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29072	Tritomaria quinquedentata	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22541	Channa argus	Species	Channidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18201	Gonimbrasia belina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27420	Venidium hirsutum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16223	Serratula xeranthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2768	Berchemia floribunda	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15341	Mucuna sloanei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22394	Hyacinthoides hispanica	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1780	Sphaeria doliolum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6899	Hepialus hecta	Species	Hepialidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15194	Euphorbia balsamifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1354	Myelochroa rhytidodes	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11629	Brassica nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9425	Punctelia microsticta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17447	Agathosma betulina	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3742	Betula maximowicziana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15904	Chrysosplenium oppositifolium	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26942	Vicoa vestita	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27425	Pseudotaxus chienii	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13410	Mcneillia graminifolia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18469	Anochetus mayri	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19200	Rolandra fruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16553	Theonella cupola	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16713	Choisya arizonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19109	Cetraria sanguinea	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8782	Arnica sachalinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16313	Ochrocarpos odoratus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13773	Eriogonum nudum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15577	Volvariella volvacea	Species	Pluteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15452	Senecio othonniformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18798	Parmelia perlata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18546	Senna longiracemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19655	Larix sukaczewii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3028	Plagius flosculosus	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
IC50	3

Activity Type	# Activity
Cell line	3

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
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	4700.0	nM	PMID[16499337]
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	8400.0	nM	PMID[16499337]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	6100.0	nM	PMID[16499337]

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 NPC151923 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	44221
0.1-0.2	5621
0.2-0.3	9
0.3-0.4	1
0.4-0.5	1
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC9611
0.6	Remote Similarity	NPC223804
0.5581	Remote Similarity	NPC474711
0.5581	Remote Similarity	NPC474588
0.5349	Remote Similarity	NPC90463

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC151923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8745
0.1-0.2	405
0.2-0.3	0
0.3-0.4	0
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