NPASS Compound

Natural Product: NPC14166

Natural Product ID	NPC14166
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HINAOCRDJFBYGD-SCZZXKLOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10877186
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

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 28 29 0 0 0 0 0 0 0 0999 V2000 -1.6779 -0.9967 1.0150 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1468 0.0361 0.0652 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2309 0.8785 -0.5166 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1198 0.8639 0.8442 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1683 0.4612 0.1911 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3263 1.3163 0.4608 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4390 -1.0266 0.3295 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4151 -1.7215 -0.5459 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3751 -0.5862 -1.0900 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6974 0.4982 -1.2732 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9131 -1.3583 1.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4442 -0.4697 1.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1712 -1.8403 0.5240 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0565 1.0882 -1.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4459 1.8040 0.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1732 0.2569 -0.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3189 1.9218 0.5461 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1715 0.6930 1.9139 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5713 2.0737 -0.2844 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1641 1.8449 1.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2419 0.6622 0.5555 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4322 -1.2013 -0.1430 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4573 -1.3775 1.3556 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8798 -2.3344 -1.3421 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2502 -2.3830 0.0512 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9570 -0.7664 -1.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1906 1.4464 -1.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4688 0.2165 -1.9662 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 6 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 2 1 0 10 5 1 0 1 11 1 0 1 12 1 0 1 13 1 0 3 14 1 0 3 15 1 0 3 16 1 0 4 17 1 0 4 18 1 0 6 19 1 0 6 20 1 0 6 21 1 0 7 22 1 0 7 23 1 0 8 24 1 0 8 25 1 0 9 26 1 6 10 27 1 0 10 28 1 0 M END

Standard InCHIKey	HINAOCRDJFBYGD-SCZZXKLOSA-N
Standard InCHI	InChI=1S/C10H18/c1-9(2)7-10(3)5-4-8(9)6-10/h8H,4-7H2,1-3H3/t8-,10+/m1/s1
SMILES	CC1(C)C[C@@]2(C)CC[C@@H]1C2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	138.14	Volume:	164.403 ? Van der Waals volume.
Dense:	0.84	LogP:	3.972 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.358 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.883 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	8.0
TPSA:	0.0 ? Topological Polar Surface Area.	H-Bond Acceptor:	0.0
H-Bond Donor:	0.0	Rings:	2.0
Heavy Atoms:	0.0

MedChem Properties

QED Drug-Likeness Score:	0.482	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.744	Fsp³:	1.0
MCE-18:	35.1 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.147	Fluc inhibitor:	0.182 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.998	Promiscuous compounds:	0.339

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.476	MDCK Permeability:	-4.726
Pgp-inhibitor:	0.746	Pgp-substrate:	0.176
PAMPA:	0.194 ? 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):	0.031
20% Bioavailability (F20%):	0.213	30% Bioavailability (F30%):	0.135
50% Bioavailability (F50%):	0.717

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.895	MRP1:	0.662
Plasma Protein Binding (PPB):	89.693%	Volume Distribution (VD):	0.47
Fu:	11.252% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.891
OATP1B3 inhibitor:	0.769	BCRP inhibitor:	0.219
BSEP inhibitor:	0.731

ADMET: Metabolism

CYP1A2-inhibitor:	0.278	CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.992	CYP2C19-substrate:	0.356
CYP2C9-inhibitor:	0.074	CYP2C9-substrate:	0.172
CYP2D6-inhibitor:	0.678	CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.905	CYP3A4-substrate:	0.864
CYP2B6-substrate:	0.94	CYP2C8-inhibitor:	0.664
HLM stability:	0.925 ? 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):

9.564

Half-life (T1/2):

0.45

ADMET: Toxicity

hERG Blockers:	0.074	hERG Blockers (10um):	0.393
Human Hepatotoxicity (H-HT):	0.601	Drug-induced Liver Injury (DILI):	0.192
AMES Toxicity:	0.507	Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.343	Skin Sensitization:	0.654
Carcinogencity:	0.747	Eye Corrosion:	0.918
Eye Irritation:	0.992	Respiratory Toxicity:	0.657
Drug-induced Neurotoxicity:	0.376	Ototoxicity:	0.264
Hematotoxicity:	0.407	Drug-induced Nephrotoxicity:	0.672
Genotoxicity:	0.05	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.086	Hek293 Cytotoxicity:	0.137
BCF:	2.715 ? 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:	4.199 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.906 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.768 ? 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
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
NPO27604	Erythrina burttii	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0031-9422(01)00459-9]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575963]
NPO27604	Erythrina burttii	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[12770595]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1294697]
NPO27878	Viola hondoensis	Species	Violaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15356999]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800637]
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	Eukaryota	roots	n.a.	n.a.	PMID[24940955]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607355]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2809609]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28134521]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32415726]
NPO27689	Mentha pulegium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33502110]
NPO27689	Mentha pulegium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34328036]
NPO27689	Mentha pulegium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37084277]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37667613]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37917799]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38005226]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38067590]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38754641]
NPO27689	Mentha pulegium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38987699]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39588261]
NPO27689	Mentha pulegium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39633960]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158155]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277307]
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27604	Erythrina burttii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28006	Pinus pumila	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28049	Piper callosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28174	Poterium sanguisorba	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16983	Persea obovatifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28191	Hardwickia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17152	Pittocaulon bombycophole	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27532	Lamprolobium fruticosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28124	Tamarix gallica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20121	Afraegle paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27480	Pinna muricata	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28305	Daphnandra johnsonii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28534	Athrixia elata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27894	Rubus pungens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4094	Aspergillus ruber	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28262	Marasmius graminum	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28512	Astragalus glycyphyllos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27681	Mikania grazielae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27861	Laggera aurita	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28074	Dianella revoluta	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27689	Mentha pulegium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28124	Tamarix gallica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27689	Mentha pulegium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27604	Erythrina burttii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14888	Pelargonium x hortorum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28433	Russula queletii	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28124	Tamarix gallica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27604	Erythrina burttii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27689	Mentha pulegium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4266	Botryotrichum murorum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27604	Erythrina burttii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27861	Laggera aurita	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28174	Poterium sanguisorba	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27480	Pinna muricata	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28499	Aethalium septicum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20121	Afraegle paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28074	Dianella revoluta	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27220	Centaurea cheiranthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27681	Mikania grazielae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28330	Colchicum arenarium	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23272	Cassinia subtropica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28321	Cortinellus berkeleyanus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28168	Armina maculata	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27334	Siphula roccellaeformis	Species	Icmadophilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9367	Jacobaea argunensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28208	Salvia dichroa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28191	Hardwickia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14888	Pelargonium x hortorum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4094	Aspergillus ruber	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28555	Adina trichotoma	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28305	Daphnandra johnsonii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28061	Gyrothyra underwoodiana	Species	Gyrothyraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27318	Sideritis lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28124	Tamarix gallica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16983	Persea obovatifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27350	Scytalidium uredinicola	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28006	Pinus pumila	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28345	Cladanthus arabicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28262	Marasmius graminum	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28253	Ceratiomyxa fruticulosa	Species	Ceratiomyxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27878	Viola hondoensis	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28512	Astragalus glycyphyllos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27532	Lamprolobium fruticosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28433	Russula queletii	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27894	Rubus pungens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28534	Athrixia elata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28049	Piper callosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17152	Pittocaulon bombycophole	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16927	Erodendrum neriifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28568	Hippeastrum aulicum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27689	Mentha pulegium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15295	Polyachyrus sphaerocephalus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28139	Umbilicaria pustulata	Species	Umbilicariaceae	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 NPC14166 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	38112
0.1-0.2	11381
0.2-0.3	345
0.3-0.4	21
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC14166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8342
0.1-0.2	784
0.2-0.3	20
0.3-0.4	4
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