NPASS Compound

Natural Product: NPC37818

Natural Product ID	NPC37818
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	INTLAWPKZQSZHS-QWUBUJLBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14731401
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002012] Oxanes

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 39 40 0 0 0 0 0 0 0 0999 V2000 5.5429 3.0185 -1.2783 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6843 2.1967 -1.4239 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6472 1.1858 -1.5796 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4900 1.2857 -0.9676 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4418 0.2688 -1.1216 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0398 -0.3894 0.1540 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0533 -1.4134 -0.1892 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0253 -2.4217 0.9437 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2335 -1.6506 2.2044 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0708 -0.1933 2.1351 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4950 0.1841 2.3072 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5015 -0.2758 1.3617 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2271 -0.4098 -0.0708 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5259 0.9300 -0.7813 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2436 0.7775 -2.2414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1910 -0.9588 -0.5932 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5110 -1.8230 2.0527 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.4984 0.4706 1.0573 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7863 -2.3938 3.6814 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.3046 3.7301 -1.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7983 0.3120 -2.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3133 2.1418 -0.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7740 -0.5383 -1.8297 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5824 0.7539 -1.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9250 -0.9279 0.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4302 -1.9702 -1.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8517 -3.1265 0.8191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9006 -3.0760 0.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3131 -1.7510 2.5290 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4587 0.2619 3.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5091 1.3070 2.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7974 -0.1987 3.3325 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3336 0.5050 1.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1256 -1.0194 -0.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9662 1.7568 -0.3119 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6008 1.1717 -0.6565 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6502 1.6450 -2.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6403 -0.1351 -2.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1746 0.7700 -2.8136 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 0 2 3 1 0 3 4 2 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 14 15 1 0 13 16 1 0 12 17 1 0 10 18 1 0 9 19 1 0 18 6 1 0 16 7 1 0 1 20 1 0 3 21 1 0 4 22 1 0 5 23 1 0 5 24 1 0 6 25 1 1 7 26 1 6 8 27 1 0 8 28 1 0 9 29 1 1 10 30 1 1 11 31 1 0 11 32 1 0 12 33 1 6 13 34 1 6 14 35 1 0 14 36 1 0 15 37 1 0 15 38 1 0 15 39 1 0 M END

Standard InCHIKey	INTLAWPKZQSZHS-QWUBUJLBSA-N
Standard InCHI	InChI=1S/C15H20Br2O2/c1-3-5-6-7-13-15-9-11(17)14(19-13)8-10(16)12(4-2)18-15/h1,5-6,10-15H,4,7-9H2,2H3/b6-5+/t10-,11-,12+,13+,14-,15+/m0/s1
SMILES	C#C/C=C/C[C@@H]1[C@H]2C[C@@H]([C@H](C[C@@H]([C@@H](CC)O2)Br)O1)Br

Calculated Properties

Physi-Chem Properties

Molecular Weight:	389.98	Volume:	299.122 ? Van der Waals volume.
Dense:	1.304	LogP:	2.718 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.973 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.052 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	13.0
TPSA:	18.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.537	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.946	Fsp³:	0.733
MCE-18:	31.385 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.828	Fluc inhibitor:	0.132 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.695	Promiscuous compounds:	0.43

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.693	MDCK Permeability:	-4.606
Pgp-inhibitor:	0.711	Pgp-substrate:	0.01
PAMPA:	0.095 ? 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):	0.0
20% Bioavailability (F20%):	0.003	30% Bioavailability (F30%):	0.006
50% Bioavailability (F50%):	0.384

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075	MRP1:	0.004
Plasma Protein Binding (PPB):	97.485%	Volume Distribution (VD):	0.215
Fu:	2.657% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.987
OATP1B3 inhibitor:	0.963	BCRP inhibitor:	0.308
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.253	CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.142	CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.996
CYP3A4-inhibitor:	0.024	CYP3A4-substrate:	0.288
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.735 ? 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):

3.206

Half-life (T1/2):

2.257

ADMET: Toxicity

hERG Blockers:	0.038	hERG Blockers (10um):	0.475
Human Hepatotoxicity (H-HT):	0.266	Drug-induced Liver Injury (DILI):	0.613
AMES Toxicity:	0.906	Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.493	Skin Sensitization:	0.948
Carcinogencity:	0.71	Eye Corrosion:	0.383
Eye Irritation:	0.945	Respiratory Toxicity:	0.965
Drug-induced Neurotoxicity:	0.749	Ototoxicity:	0.463
Hematotoxicity:	0.14	Drug-induced Nephrotoxicity:	0.397
Genotoxicity:	0.358	RPMI-8226 Immunitoxicity:	0.142
A549 Cytotoxicity:	0.115	Hek293 Cytotoxicity:	0.408
BCF:	1.47 ? 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:	3.925 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.394 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.954 ? 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
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792422]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17343407]
NPO8996	Aplysina gerardogreeni	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512741]
NPO17974	Sarcophyton subviride	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27704808]
NPO19344	Sporormiella teretispora	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760082]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1550	Talaromyces purpureogenus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10038.2	Abies pinsapo var. tazaotana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27685	Abuta concolor	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14030	Alcyonium paessleri	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19140	Aloe excelsa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22229	Alternaria botrytis	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8996	Aplysina gerardogreeni	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28880	Aquilegia coerulea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19739	Astragalus alexandri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3680	Beilschmiedia obtusifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10706	Bergenia hissarica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19544	Camassia cusickii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12767	Cassipourea gummiflua	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18477	Celastrus scandens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17559	Coespeletia lutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3608	Eleutherococcus giraldii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16666	Eunicea calyculata	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17672	Euryops linifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20433	Garuga gamblei	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17309	Halfordia scleroxyla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16892	Helogyne hutchisonii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13566	Hypoxylon serpens	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16219	Hyssopus lophanthoides	Species	Eulophidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13137	Isodon flexicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18964	Iva hayesiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25617	Lactococcus lactis	Species	Streptococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19480	Laurencia nipponica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14318	Lespedeza davidii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14511	Lespedeza striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18394	Linaria purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27736	Melanochromis auratus	Species	Cichlidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15695	Mikania vitifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1998	Premna serratifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16528	Psydrax dicoccos	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19053	Pteris formosana	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO647	Rhodotorula glutinis	Species	Sporidiobolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18567	Salvia clevelandi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1192	Salvia corrugata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18308	Saponaria officinalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17974	Sarcophyton subviride	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7040	Sinularia parva	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3628	Solanum aethiopicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17173	Sporobolus alterniflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19344	Sporormiella teretispora	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18891	Stevia potrerensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16010	Synoicum prunum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17429	Teucrium creticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17546	Torulaspora delbrueckii	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18308	Saponaria officinalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18477	Celastrus scandens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3608	Eleutherococcus giraldii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18477	Celastrus scandens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13137	Isodon flexicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18308	Saponaria officinalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19480	Laurencia nipponica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19739	Astragalus alexandri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17309	Halfordia scleroxyla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22229	Alternaria botrytis	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19544	Camassia cusickii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17546	Torulaspora delbrueckii	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19480	Laurencia nipponica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1550	Talaromyces purpureogenus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7040	Sinularia parva	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO647	Rhodotorula glutinis	Species	Sporidiobolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18567	Salvia clevelandi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3628	Solanum aethiopicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1998	Premna serratifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25617	Lactococcus lactis	Species	Streptococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17559	Coespeletia lutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15695	Mikania vitifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16666	Eunicea calyculata	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18394	Linaria purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8996	Aplysina gerardogreeni	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16219	Hyssopus lophanthoides	Species	Eulophidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18308	Saponaria officinalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16010	Synoicum prunum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3608	Eleutherococcus giraldii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19140	Aloe excelsa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14511	Lespedeza striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27736	Melanochromis auratus	Species	Cichlidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13137	Isodon flexicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14318	Lespedeza davidii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16528	Psydrax dicoccos	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1192	Salvia corrugata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19344	Sporormiella teretispora	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16892	Helogyne hutchisonii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27685	Abuta concolor	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17173	Sporobolus alterniflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17974	Sarcophyton subviride	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19053	Pteris formosana	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20433	Garuga gamblei	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3680	Beilschmiedia obtusifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12767	Cassipourea gummiflua	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14030	Alcyonium paessleri	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17672	Euryops linifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13566	Hypoxylon serpens	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10038.2	Abies pinsapo var. tazaotana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17429	Teucrium creticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18964	Iva hayesiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28880	Aquilegia coerulea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10706	Bergenia hissarica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18477	Celastrus scandens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18891	Stevia potrerensis	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 NPC37818 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	36337
0.1-0.2	13440
0.2-0.3	69
0.3-0.4	6
0.4-0.5	2
0.5-0.6	0
0.6-0.7	2
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8286	Intermediate Similarity	NPC271000
0.8286	Intermediate Similarity	NPC473306
0.6977	Remote Similarity	NPC473453
0.6923	Remote Similarity	NPC52781

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC37818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7951
0.1-0.2	1199
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