NPASS Compound

Natural Product: NPC277525

Natural Product ID	NPC277525
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Coronarin E
IUPAC Name	3-[(E)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]furan
Synonyms	Coranorin E; Coronarin E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL109252
PubChem CID	9971144
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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 49 51 0 0 0 0 0 0 0 0999 V2000 1.1849 2.8771 1.1703 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3618 2.0684 0.4944 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7775 2.6364 -0.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9920 1.7633 -0.2604 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7040 0.3242 0.0878 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3094 -0.0960 -0.3486 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6381 0.6199 0.5405 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0574 0.2771 0.4429 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6509 -0.4404 -0.4645 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0851 -0.6708 -0.3876 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8245 -1.4073 -1.2804 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0585 -1.3869 -0.8841 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2018 -0.6914 0.2081 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9765 -0.2121 0.5688 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0651 0.2500 -1.7971 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2041 -1.5747 -0.0563 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2287 -2.0416 0.9776 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6360 -1.8948 0.4667 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7970 -0.6056 -0.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1021 0.0851 0.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9357 -0.9219 -1.7414 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9964 3.9642 1.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0199 2.5089 1.7316 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0252 3.6181 0.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4439 2.9495 -1.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7265 2.1751 0.4623 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4679 1.8300 -1.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6612 0.2874 1.2014 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3474 0.3207 1.6015 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6929 0.6758 1.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0989 -0.8550 -1.2573 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4154 -1.9062 -2.1547 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1270 -0.5199 0.7410 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7045 0.3997 1.4120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7555 0.9905 -1.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9687 0.8012 -2.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0541 -0.6085 -2.4614 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2156 -2.2163 -0.9425 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7766 -1.7812 0.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0378 -3.1262 1.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0484 -1.5598 1.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9427 -2.7592 -0.1562 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2988 -1.8357 1.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9577 0.6511 1.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3868 0.8288 -0.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8738 -0.6916 0.2415 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2134 -0.0155 -2.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1419 -1.5186 -2.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8662 -1.5650 -1.8287 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 2 0 6 15 1 6 6 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 7 2 1 0 14 10 1 0 19 5 1 0 1 22 1 0 1 23 1 0 3 24 1 0 3 25 1 0 4 26 1 0 4 27 1 0 5 28 1 1 7 29 1 1 8 30 1 0 9 31 1 0 11 32 1 0 13 33 1 0 14 34 1 0 15 35 1 0 15 36 1 0 15 37 1 0 16 38 1 0 16 39 1 0 17 40 1 0 17 41 1 0 18 42 1 0 18 43 1 0 20 44 1 0 20 45 1 0 20 46 1 0 21 47 1 0 21 48 1 0 21 49 1 0 M END

Standard InCHIKey	QXVXYNOIXUIXBI-NDLVVHCESA-N
Standard InCHI	InChI=1S/C20H28O/c1-15-6-9-18-19(2,3)11-5-12-20(18,4)17(15)8-7-16-10-13-21-14-16/h7-8,10,13-14,17-18H,1,5-6,9,11-12H2,2-4H3/b8-7+/t17-,18-,20+/m0/s1
SMILES	C=C1CC[C@@H]2[C@]([C@H]1/C=C/c1cocc1)(C)CCCC2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	284.21	Volume:	327.051 ? Van der Waals volume.
Dense:	0.869	LogP:	5.022 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.814 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.629 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	18.0
TPSA:	13.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.599	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.075	Fsp³:	0.6
MCE-18:	67.688 ? 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:	0.489	Fluc inhibitor:	0.674 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.658	Promiscuous compounds:	0.066

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.631	MDCK Permeability:	-4.74
Pgp-inhibitor:	0.816	Pgp-substrate:	0.001
PAMPA:	0.004 ? 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):	0.004
20% Bioavailability (F20%):	0.075	30% Bioavailability (F30%):	0.373
50% Bioavailability (F50%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167	MRP1:	0.142
Plasma Protein Binding (PPB):	98.571%	Volume Distribution (VD):	0.466
Fu:	1.328% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.915
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.767	CYP1A2-substrate:	0.526
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.18	CYP2C9-substrate:	0.824
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.293
CYP3A4-inhibitor:	0.15	CYP3A4-substrate:	0.989
CYP2B6-substrate:	0.023	CYP2C8-inhibitor:	0.864
HLM stability:	0.996 ? 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):

9.949

Half-life (T1/2):

0.596

ADMET: Toxicity

hERG Blockers:	0.243	hERG Blockers (10um):	0.515
Human Hepatotoxicity (H-HT):	0.535	Drug-induced Liver Injury (DILI):	0.791
AMES Toxicity:	0.3	Rat Oral Acute Toxicity:	0.552
Maximum Recommended Daily Dose:	0.909	Skin Sensitization:	0.75
Carcinogencity:	0.599	Eye Corrosion:	0.085
Eye Irritation:	0.982	Respiratory Toxicity:	0.82
Drug-induced Neurotoxicity:	0.461	Ototoxicity:	0.29
Hematotoxicity:	0.162	Drug-induced Nephrotoxicity:	0.413
Genotoxicity:	0.373	RPMI-8226 Immunitoxicity:	0.088
A549 Cytotoxicity:	0.154	Hek293 Cytotoxicity:	0.498
BCF:	3.072 ? 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:	4.862 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.726 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.78 ? 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
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np100392m]
NPO26456	Jaborosa leucotricha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517742]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	Kampaengsaen district, Nakhon Pathom province, Thailand	n.a.	PMID[18554915]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[19027298]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19332371]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19782567]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20196571]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21106458]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23422227]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23910596]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.70 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.53 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.55 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.48 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.49 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.47 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.73 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.50 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.52 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.74 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.75 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.57 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.58 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.56 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.54 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.51 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.72 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	Seeds	Djanga (10.37 N; 4.47 W) and BÃƒÂ©rÃƒÂ©gadougou (10.49 N; 4.76 W) villages in the Southwest of Burkina Faso.		PMID[24566330]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33396533]
NPO42048	Rhynchanthus beesianus	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33997008]
NPO21639	Prunus mahaleb	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34382873]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35481430]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37514241]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39317685]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176399]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21639	Prunus mahaleb	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26610	Spiraea formosana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26208	Brombya platynema	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25906	Acacia linarioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25582	Aquilegia viridiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26079	Asterococcus muratae	Species	Cerococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26481	Astragalus kabadianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24733	Celastrus dispermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26524	Chondria californica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26816	Clinopodium gracile	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25393	Coelogyne flavida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26676	Daphne arisanensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24608	Gaertnera morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15693	Guadua angustifolia	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26846	Guettarda noumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24829	Gyrostroma missouriense	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26554	Hexagonia speciosa	Species	Carabidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29093	Homalium longifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26456	Jaborosa leucotricha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10372	Kiggelaria africana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26743	Lippia adoensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22353	Lucilia caesar	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24894	Parmelia tinctina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23589	Pecten irradians	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13051	Perymenium jelskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19916	Phenax angustifolius	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26392	Piptadenia colubrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14283	Ponera metallica	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23410	Potentilla candicans	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26306	Pyrobaculum organotrophum	Species	Thermoproteaceae	Archaea	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13072	Rhamnus formosana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25768	Senecio ruwenzoriensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17771	Senna didymobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26175	Spongionella gracilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25996	Stenolobium stans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25575	Streptomyces pseudovenezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25803	Strychnos elaeocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26357	Trachyrhamphus serratus	Species	Syngnathidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25732	Trichilia havanensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7465	Vachellia leucophloea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28819	Veronica liwanensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25086	Viburnum betulifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	Leaves	n.a.		Database[FooDB]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25803	Strychnos elaeocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26610	Spiraea formosana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5704	Pecten caurinus	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26816	Clinopodium gracile	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26306	Pyrobaculum organotrophum	Species	Thermoproteaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO24894	Parmelia tinctina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25906	Acacia linarioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7465	Vachellia leucophloea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13072	Rhamnus formosana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24608	Gaertnera morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26676	Daphne arisanensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26208	Brombya platynema	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25732	Trichilia havanensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14283	Ponera metallica	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26392	Piptadenia colubrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25582	Aquilegia viridiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19916	Phenax angustifolius	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25575	Streptomyces pseudovenezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26743	Lippia adoensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24829	Gyrostroma missouriense	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23589	Pecten irradians	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10372	Kiggelaria africana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25768	Senecio ruwenzoriensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26846	Guettarda noumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21639	Prunus mahaleb	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29093	Homalium longifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26357	Trachyrhamphus serratus	Species	Syngnathidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26481	Astragalus kabadianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15693	Guadua angustifolia	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23410	Potentilla candicans	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26524	Chondria californica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25086	Viburnum betulifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26079	Asterococcus muratae	Species	Cerococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28819	Veronica liwanensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26175	Spongionella gracilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13051	Perymenium jelskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26456	Jaborosa leucotricha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17771	Senna didymobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24733	Celastrus dispermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25996	Stenolobium stans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26554	Hexagonia speciosa	Species	Carabidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25803	Strychnos elaeocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25393	Coelogyne flavida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22353	Lucilia caesar	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26610	Spiraea formosana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11542	Laminaria cloustoni	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7302	Glycosmis parva	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6584	Pterodon apparicioi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	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
NPO42048	Rhynchanthus beesianus	Oil	n.a.	0.3	n.a.	n.a.	%	PMID[33997008]

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	7
FC	1
Activity	1

Activity Type	# Activity
Cell line	9

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
NPT168	Cell line	P388	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[9873721]
NPT319	Cell line	B16	Mus musculus	IC50	=	18.8	ug.mL-1	PMID[9873721]
NPT788	Cell line	SNU1	Homo sapiens	IC50	=	8.0	ug.mL-1	PMID[9873721]
NPT1970	Cell line	THP-1	Homo sapiens	IC50	=	33990.0	nM	PMID[19782567]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	31210.0	nM	PMID[19782567]
NPT1083	Cell line	A-375	Homo sapiens	IC50	=	36580.0	nM	PMID[19782567]
NPT81	Cell line	A549	Homo sapiens	IC50	=	53260.0	nM	PMID[19782567]
NPT111	Cell line	K562	Homo sapiens	FC	=	0.7	n.a.	PMID[20196571]
NPT111	Cell line	K562	Homo sapiens	Activity	=	87.2	%	PMID[20196571]

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 NPC277525 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	24455
0.1-0.2	23745
0.2-0.3	1488
0.3-0.4	152
0.4-0.5	10
0.5-0.6	5
0.6-0.7	2
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
0.6727	Remote Similarity	NPC300098
0.6545	Remote Similarity	NPC290193
0.5593	Remote Similarity	NPC87466
0.541	Remote Similarity	NPC246392
0.5238	Remote Similarity	NPC290955
0.5156	Remote Similarity	NPC208389
0.5156	Remote Similarity	NPC26532

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC277525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6052
0.1-0.2	3056
0.2-0.3	41
0.3-0.4	1
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