NPASS Compound

Natural Product: NPC7133

Natural Product ID	NPC7133
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WGPCZPLRVAWXPW-LLVKDONJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10888889
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

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 36 36 0 0 0 0 0 0 0 0999 V2000 4.2245 1.0476 0.0681 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1869 -0.3326 0.6203 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8676 -1.0096 0.6417 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1655 -1.2359 -0.6360 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7020 -0.0494 -1.4092 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6856 0.7662 -0.6594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5840 -0.0365 -0.3427 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5518 0.8700 0.3973 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8118 0.1451 0.7352 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5382 -0.3706 -0.4893 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9439 -0.5523 0.1017 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0427 0.6811 0.9154 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0794 1.2969 1.2432 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7582 1.0550 1.2665 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6191 1.0501 -0.9840 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3069 1.6341 0.1306 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9865 1.6856 0.6333 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9614 -0.9463 0.0645 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6241 -0.2997 1.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1393 -0.4647 1.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9552 -2.0147 1.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2455 -1.8494 -0.4030 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7696 -1.9280 -1.3223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1349 -0.4893 -2.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4950 0.5791 -1.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3826 1.6629 -1.2317 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0654 1.1330 0.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3300 -0.8788 0.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0469 -0.4445 -1.2609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0690 1.1731 1.3452 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7473 1.7724 -0.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6154 -0.7139 1.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1271 -1.3097 -0.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6588 0.4165 -1.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7082 -0.6261 -0.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9050 -1.4165 0.7843 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 9 1 0 1 15 1 0 1 16 1 0 1 17 1 0 2 18 1 0 2 19 1 0 3 20 1 0 3 21 1 0 4 22 1 0 4 23 1 0 5 24 1 0 5 25 1 0 6 26 1 0 6 27 1 0 7 28 1 0 7 29 1 0 8 30 1 0 8 31 1 0 9 32 1 1 10 33 1 0 10 34 1 0 11 35 1 0 11 36 1 0 M END

Standard InCHIKey	WGPCZPLRVAWXPW-LLVKDONJSA-N
Standard InCHI	InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-11-9-10-12(13)14-11/h11H,2-10H2,1H3/t11-/m1/s1
SMILES	CCCCCCCC[C@@H]1CCC(=O)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	198.16	Volume:	222.496 ? Van der Waals volume.
Dense:	0.891	LogP:	4.017 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.239 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.869 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	6.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.462	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.624	Fsp³:	0.917
MCE-18:	11.304 ? 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:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.081	Fluc inhibitor:	0.049 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.999	Promiscuous compounds:	0.512

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.021	MDCK Permeability:	-4.748
Pgp-inhibitor:	0.16	Pgp-substrate:	0.343
PAMPA:	0.051 ? 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):	0.266
20% Bioavailability (F20%):	0.427	30% Bioavailability (F30%):	0.767
50% Bioavailability (F50%):	0.486

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12	MRP1:	0.946
Plasma Protein Binding (PPB):	98.14%	Volume Distribution (VD):	0.766
Fu:	2.857% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.464
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.697
BSEP inhibitor:	0.528

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.125	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.797
CYP3A4-inhibitor:	0.437	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.826
HLM stability:	0.068 ? 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):

5.569

Half-life (T1/2):

0.545

ADMET: Toxicity

hERG Blockers:	0.145	hERG Blockers (10um):	0.535
Human Hepatotoxicity (H-HT):	0.55	Drug-induced Liver Injury (DILI):	0.367
AMES Toxicity:	0.246	Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.193	Skin Sensitization:	0.983
Carcinogencity:	0.49	Eye Corrosion:	0.994
Eye Irritation:	0.998	Respiratory Toxicity:	0.63
Drug-induced Neurotoxicity:	0.371	Ototoxicity:	0.175
Hematotoxicity:	0.263	Drug-induced Nephrotoxicity:	0.629
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.185	Hek293 Cytotoxicity:	0.054
BCF:	1.111 ? 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:	3.587 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.136 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.356 ? 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
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[10670815]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038554]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[17226159]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17237222]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	Malatya Fruit Research Institute	between the first and third weeks of 2005-Jul.	PMID[18038980]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18044840]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21381684]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21381684]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	stem	n.a.	PMID[21381684]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22187429]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23784883]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24400858]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26934105]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[27133212]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7792	Coreopsis grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15434	Rhodomicrobium vannielii	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13740	Aconitum kamtschaticum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16109	Actinidia kolomikta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15679	Amyris marshii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12470	Brachyspira hyodysenteriae	Species	Brachyspiraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7077	Canarium strictum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15312	Coelogorgia palmosa	Species	Coelogorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14604	Dipteronia dyeriana	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9386	Ectropis bicolor	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14914	Esox saurus	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11962	Garcinia macrophylla	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14442	Gouania microcarpa	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13582	Leucopaxillus giganteus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13273	Maytenus loeseneri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5750	Monomorium floricola	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10452	Odontites rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3697	Ongokea klaineana	Species	Aptandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2607	Ophiorrhiza blumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16625	Phalaenopsis aphrodite	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8671	Physalis solanaceus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15570	Plectranthus mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15159	Podocarpus salignus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11644	Prosopis ruscifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15178	Psychotria bahiensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16311	Rusavskia elegans	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11376	Schistostephium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1723	Sideritis syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12457	Siphocampylus verticillatus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22056.1	Streptomyces fervens	Subspecies	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12951	Talaromyces coalescens	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14747	Usnea florida	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22053	Vepris pilosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16541	Veratrum stenophyllum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12547	Viburnum chingii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26256	Zanthoxylum chiriquinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13740	Aconitum kamtschaticum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15679	Amyris marshii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15570	Plectranthus mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16625	Phalaenopsis aphrodite	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16541	Veratrum stenophyllum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16311	Rusavskia elegans	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12470	Brachyspira hyodysenteriae	Species	Brachyspiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15434	Rhodomicrobium vannielii	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15159	Podocarpus salignus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12547	Viburnum chingii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13582	Leucopaxillus giganteus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12951	Talaromyces coalescens	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11644	Prosopis ruscifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12457	Siphocampylus verticillatus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13273	Maytenus loeseneri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9386	Ectropis bicolor	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10452	Odontites rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8671	Physalis solanaceus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16109	Actinidia kolomikta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22056.1	Streptomyces fervens	Subspecies	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14604	Dipteronia dyeriana	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2607	Ophiorrhiza blumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3697	Ongokea klaineana	Species	Aptandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14747	Usnea florida	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22053	Vepris pilosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7077	Canarium strictum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7792	Coreopsis grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11376	Schistostephium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14914	Esox saurus	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1723	Sideritis syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26256	Zanthoxylum chiriquinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5750	Monomorium floricola	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15312	Coelogorgia palmosa	Species	Coelogorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15178	Psychotria bahiensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11962	Garcinia macrophylla	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14442	Gouania microcarpa	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27572	Sophora subprostrata	Species	Fabaceae	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 NPC7133 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	23738
0.1-0.2	23033
0.2-0.3	2605
0.3-0.4	391
0.4-0.5	60
0.5-0.6	16
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC63182
1.0	High Similarity	NPC145045
1.0	High Similarity	NPC52700
0.95	High Similarity	NPC105329
0.9091	High Similarity	NPC603863
0.8571	High Similarity	NPC273545
0.8182	Intermediate Similarity	NPC326957
0.7619	Intermediate Similarity	NPC176500
0.7143	Intermediate Similarity	NPC94368
0.6667	Remote Similarity	NPC47363
0.6667	Remote Similarity	NPC287231
0.6667	Remote Similarity	NPC314084
0.6207	Remote Similarity	NPC489810
0.6	Remote Similarity	NPC478976
0.5517	Remote Similarity	NPC23155
0.5455	Remote Similarity	NPC321699
0.5333	Remote Similarity	NPC609089
0.5294	Remote Similarity	NPC481557
0.5294	Remote Similarity	NPC481560
0.5294	Remote Similarity	NPC481652
0.5294	Remote Similarity	NPC481651
0.52	Remote Similarity	NPC201622
0.52	Remote Similarity	NPC305660
0.52	Remote Similarity	NPC12156
0.52	Remote Similarity	NPC161097
0.52	Remote Similarity	NPC28598
0.52	Remote Similarity	NPC22903
0.52	Remote Similarity	NPC54980
0.5161	Remote Similarity	NPC55678
0.5143	Remote Similarity	NPC470436

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC7133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6700
0.1-0.2	2260
0.2-0.3	175
0.3-0.4	10
0.4-0.5	3
0.5-0.6	1
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6667	Remote Similarity	NPD2699	Pre-clinical
0.5161	Remote Similarity	NPD6125	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data