NPASS Compound

Natural Product: NPC109854

Natural Product ID	NPC109854
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RWWVEQKPFPXLGL-ONCXSQPRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	221062
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 52 54 0 0 0 0 0 0 0 0999 V2000 4.7449 0.3087 -1.6463 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6184 -0.3976 -0.3098 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2881 0.4171 0.7615 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1885 -0.5417 -0.0041 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5978 -1.7024 0.1789 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1863 -1.9374 0.4829 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3837 -0.7401 0.6508 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0594 0.5248 0.4346 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3223 0.6217 0.1412 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2974 1.8344 0.5289 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9476 1.6348 -0.3323 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6849 0.4588 0.2736 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9709 -0.7947 -0.0779 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7916 -1.0540 -1.5375 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7024 -1.9716 0.5238 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0134 -1.5900 1.1717 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8174 -0.8059 0.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1428 0.5164 -0.0283 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4428 1.1264 -1.3825 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7563 1.4550 0.9750 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6549 1.0844 1.7772 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3727 2.7876 1.0817 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7968 0.4245 -1.9593 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1550 -0.3167 -2.3777 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1930 1.2605 -1.5660 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0564 -1.4240 -0.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3798 1.4557 0.3887 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7142 0.4421 1.7093 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2969 0.0074 0.9676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2880 -2.5828 0.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7884 -2.5393 -0.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1836 -2.6290 1.3810 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0989 -0.7228 1.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7678 1.6384 -0.0068 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 2.6798 0.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0320 2.0394 1.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5757 2.5434 -0.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6108 1.4181 -1.3704 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5760 0.5729 1.3933 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7095 -0.7112 -2.0812 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7585 -2.1533 -1.6953 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1146 -0.5773 -1.9641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9467 -2.7453 -0.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1170 -2.5065 1.3054 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9030 -1.0794 2.1273 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5647 -2.5339 1.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8427 -0.6854 0.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9444 -1.3952 -0.7479 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8882 0.2911 -1.9979 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2402 1.8972 -1.3389 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5776 1.5807 -1.8703 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7816 3.4195 1.7345 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 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 2 0 20 22 1 0 9 4 1 0 18 12 1 0 13 7 1 0 1 23 1 0 1 24 1 0 1 25 1 0 2 26 1 0 3 27 1 0 3 28 1 0 3 29 1 0 5 30 1 0 6 31 1 0 6 32 1 0 7 33 1 1 9 34 1 0 10 35 1 0 10 36 1 0 11 37 1 0 11 38 1 0 12 39 1 1 14 40 1 0 14 41 1 0 14 42 1 0 15 43 1 0 15 44 1 0 16 45 1 0 16 46 1 0 17 47 1 0 17 48 1 0 19 49 1 0 19 50 1 0 19 51 1 0 22 52 1 0 M END

Standard InCHIKey	RWWVEQKPFPXLGL-ONCXSQPRSA-N
Standard InCHI	InChI=1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,12-13,16-17H,5,7-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1
SMILES	CC(C)C1=CC[C@H]2C(=C1)CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	302.22	Volume:	338.478 ? Van der Waals volume.
Dense:	0.893	LogP:	4.552 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.502 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.104 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	17.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.76	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.194	Fsp³:	0.75
MCE-18:	54.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.503	Fluc inhibitor:	0.11 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.011 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.851	Promiscuous compounds:	0.028

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.887	MDCK Permeability:	-4.92
Pgp-inhibitor:	0.855	Pgp-substrate:	0.003
PAMPA:	0.458 ? 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):	0.006
20% Bioavailability (F20%):	0.057	30% Bioavailability (F30%):	0.044
50% Bioavailability (F50%):	0.341

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.989
Plasma Protein Binding (PPB):	97.677%	Volume Distribution (VD):	-0.234
Fu:	2.714% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.971	BCRP inhibitor:	0.003
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.901	CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.896	CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.662	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.986
CYP2B6-substrate:	0.053	CYP2C8-inhibitor:	1.0
HLM stability:	0.402 ? 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):

3.259

Half-life (T1/2):

0.722

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.078
Human Hepatotoxicity (H-HT):	0.65	Drug-induced Liver Injury (DILI):	0.448
AMES Toxicity:	0.099	Rat Oral Acute Toxicity:	0.186
Maximum Recommended Daily Dose:	0.407	Skin Sensitization:	0.963
Carcinogencity:	0.634	Eye Corrosion:	0.79
Eye Irritation:	0.936	Respiratory Toxicity:	0.753
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.51
Hematotoxicity:	0.46	Drug-induced Nephrotoxicity:	0.813
Genotoxicity:	0.296	RPMI-8226 Immunitoxicity:	0.04
A549 Cytotoxicity:	0.018	Hek293 Cytotoxicity:	0.052
BCF:	1.674 ? 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:	4.178 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.496 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.971 ? 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]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124753]
NPO2669	Bowdichia virgilioides	Species	Fabaceae	Eukaryota	n.a.	xylem	n.a.	PMID[16286304]
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]
NPO2669	Bowdichia virgilioides	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[29182338]
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]
NPO8443	Uvaria microcarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37531297]
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]
NPO4844	Acacia simplicifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2669	Bowdichia virgilioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1406	Centaurea zuccariniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8962	Cousinia canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8140	Nauclea parva	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5752	Pholas dactylus	Species	Pholadidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5365	Tetradenia glauca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9947	Teucrium scorodonia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2905	Tinospora hainanensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21689	Titanotrichum oldhamii	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8443	Uvaria microcarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4037	Veronica anagallis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1255	Waitzia acuminata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3463	Wrightia tinctoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6937	Xylaria hypoxylon	Species	Xylariaceae	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]
NPO2905	Tinospora hainanensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28124	Tamarix gallica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12068	Firmiana simplex	Species	Malvaceae	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]
NPO12068	Firmiana simplex	Species	Malvaceae	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]
NPO2905	Tinospora hainanensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28124	Tamarix gallica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9947	Teucrium scorodonia	Species	Lamiaceae	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]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO9947	Teucrium scorodonia	Species	Lamiaceae	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]
NPO21689	Titanotrichum oldhamii	Species	Gesneriaceae	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]
NPO23907	Grazielia serrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2905	Tinospora hainanensis	Species	Menispermaceae	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]
NPO8413	Echinus auritus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16983	Persea obovatifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3463	Wrightia tinctoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27350	Scytalidium uredinicola	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12068	Firmiana simplex	Species	Malvaceae	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]
NPO4844	Acacia simplicifolia	Species	Fabaceae	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]
NPO11409	Trichothecium sympodiale	Species	n.a.	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]
NPO2669	Bowdichia virgilioides	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]
NPO8443	Uvaria microcarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8140	Nauclea parva	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28433	Russula queletii	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5365	Tetradenia glauca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27894	Rubus pungens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6937	Xylaria hypoxylon	Species	Xylariaceae	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]
NPO1406	Centaurea zuccariniana	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]
NPO8962	Cousinia canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1255	Waitzia acuminata	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]
NPO5752	Pholas dactylus	Species	Pholadidae	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]
NPO4037	Veronica anagallis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13209	Strychnos tomentosa	Species	Loganiaceae	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	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT946	Individual protein	ATP-citrate synthase	Homo sapiens	IC50	>	40000.0	nM	PMID[37196240]

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 NPC109854 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Natural Product ID

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC109854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Drug ID	Developmental Stage

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data