NPASS Compound

Natural Product: NPC149505

Natural Product ID	NPC149505
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Beta-Peltatin-A Methylether
IUPAC Name	(5aR,8aR,9R)-4-methoxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
Synonyms	Beta-Peltatin A Methyl Ether; Beta-Peltatin-A Methylether
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL483004
PubChem CID	159962
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

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 55 59 0 0 0 0 0 0 0 0999 V2000 4.2764 0.4681 3.1520 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4123 -0.3022 1.9740 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3541 -0.3423 1.0566 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1963 0.3436 1.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1055 0.3429 0.3949 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2711 -0.4178 -0.7433 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4292 -1.1350 -1.0119 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4483 -1.0841 -0.1081 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6209 -1.7919 -0.3494 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6407 -1.1054 -1.0632 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5563 -1.8884 -2.1696 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4782 -1.9189 -3.0865 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1243 1.1058 0.7164 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3459 0.2587 0.7601 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4025 -0.7910 1.6545 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5149 -1.6240 1.7523 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5997 -1.4216 0.9516 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5507 -0.3647 0.0463 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4453 0.4560 -0.0446 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5096 1.5540 -1.0553 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1334 2.0547 -1.3912 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1277 3.4910 -1.8979 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2502 3.8246 -1.6462 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7526 3.0524 -0.6107 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9340 3.0222 -0.2208 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4041 2.2943 -0.0907 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6501 -0.1676 -0.7581 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8336 -0.7568 -2.0243 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5576 -2.3860 1.2540 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2216 -2.9761 2.4967 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8210 -2.7285 2.5521 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9568 1.5160 2.9067 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5115 0.0645 3.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2674 0.5984 3.6569 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1389 0.9280 2.2047 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4696 -0.4780 -1.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1622 -0.3646 -0.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2436 -0.5559 -1.9418 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3814 -1.8556 -1.4429 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2402 -0.9182 -3.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5637 -2.2978 -2.5689 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6680 -2.6047 -3.9211 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0652 1.5102 1.7835 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5752 -1.0263 2.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9442 1.1047 -1.9716 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1342 2.3919 -0.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5969 1.4772 -2.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3873 3.5771 -2.9534 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7378 4.0858 -1.2069 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0863 2.9571 0.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0286 0.0719 -2.7394 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9251 -1.2773 -2.3947 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6922 -1.4405 -2.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3767 -4.0721 2.4955 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6680 -2.4576 3.3512 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 7 11 1 0 11 12 1 0 5 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 18 27 1 0 27 28 1 0 17 29 1 0 29 30 1 0 30 31 1 0 8 3 1 0 26 13 1 0 19 14 1 0 26 21 1 0 31 16 1 0 1 32 1 0 1 33 1 0 1 34 1 0 4 35 1 0 6 36 1 0 10 37 1 0 10 38 1 0 10 39 1 0 12 40 1 0 12 41 1 0 12 42 1 0 13 43 1 1 15 44 1 0 20 45 1 0 20 46 1 0 21 47 1 6 22 48 1 0 22 49 1 0 26 50 1 1 28 51 1 0 28 52 1 0 28 53 1 0 30 54 1 0 30 55 1 0 M END

Standard InCHIKey	BFKORKXLSJUYSS-RQUSPXKASA-N
Standard InCHI	InChI=1S/C23H24O8/c1-25-15-6-11(7-16(26-2)21(15)28-4)18-13-8-17-22(31-10-30-17)20(27-3)14(13)5-12-9-29-23(24)19(12)18/h6-8,12,18-19H,5,9-10H2,1-4H3/t12-,18+,19-/m0/s1
SMILES	COc1cc(cc(c1OC)OC)[C@@H]1c2cc3c(c(c2C[C@H]2COC(=O)[C@H]12)OC)OCO3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	428.15	Volume:	415.448 ? Van der Waals volume.
Dense:	1.031	LogP:	2.145 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.345 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.712 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	26.0
TPSA:	81.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.673	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.736	Fsp³:	0.435
MCE-18:	94.182 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.22	Fluc inhibitor:	0.221 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.355 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.132 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.222	Promiscuous compounds:	0.416

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.899	MDCK Permeability:	-4.741
Pgp-inhibitor:	0.079	Pgp-substrate:	0.001
PAMPA:	0.045 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999	MRP1:	0.998
Plasma Protein Binding (PPB):	97.174%	Volume Distribution (VD):	-0.015
Fu:	2.825% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.411
OATP1B3 inhibitor:	0.345	BCRP inhibitor:	0.001
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.962	CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.144
HLM stability:	0.098 ? 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):

5.217

Half-life (T1/2):

1.715

ADMET: Toxicity

hERG Blockers:	0.21	hERG Blockers (10um):	0.621
Human Hepatotoxicity (H-HT):	0.919	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.781	Rat Oral Acute Toxicity:	0.902
Maximum Recommended Daily Dose:	0.826	Skin Sensitization:	0.99
Carcinogencity:	0.91	Eye Corrosion:	0.001
Eye Irritation:	0.315	Respiratory Toxicity:	0.973
Drug-induced Neurotoxicity:	0.965	Ototoxicity:	0.715
Hematotoxicity:	0.958	Drug-induced Nephrotoxicity:	0.982
Genotoxicity:	0.993	RPMI-8226 Immunitoxicity:	0.695
A549 Cytotoxicity:	0.903	Hek293 Cytotoxicity:	0.801
BCF:	1.809 ? 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:	3.953 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.455 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.576 ? 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
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94598-9]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2225/vol5-issue3-fulltext-4]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325242]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088440]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713420]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15009205]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038560]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933860]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21500777]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25323720]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	rhizomes	Liaoning province, China	2011-SEP	PMID[25927664]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26731565]
NPO8247	Austrobaileya scandens	Species	Austrobaileyaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27214307]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31419126]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32078653]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35889256]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37241721]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37800169]
NPO23682	Juniperus phoenicea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38263385]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38370080]
NPO23682	Juniperus phoenicea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39345860]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39684509]
NPO23682	Juniperus phoenicea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6253598]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12785	Bursera fagaroides	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12801	Aglaia meridionalis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18061	Anacystis cyanea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17718	Artemisia schmidtiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19189	Brickellia pendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18377	Chaetomium retardatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17275	Chamaemelum scariosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3050	Cladonia pseudodidyma	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21938	Coleus carnosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18847	Copaifera paupera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9535	Cortinarius basirubescens	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18792	Crotalaria lechnaultii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16829	Dunaliella acidophila	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12072	Escallonia philippiana	Species	Escalloniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17596	Ficus maxima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18242	Gleichenia glauca	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18520	Helipterum strictum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3746	Hesperocyparis nevadensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13594	Hippocratea indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11677	Lactobacillus acidophilus	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11603	Lathyrus macrorrhizus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19057	Lentinellus omphalodes	Species	Auriscalpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18575	Ochtodes crockeri	Species	Rhizophyllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12282	Parmelia conspersa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7807	Polyporus sulphureus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18173	Pyrocystis lunula	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17190	Senecio erraticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10712	Tabebuia rosea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17068	Talaromyces wortmanni	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15608	Tanacetum santolina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17709	Timonius kaniensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23682	Juniperus phoenicea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3158	Linum album	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8247	Austrobaileya scandens	Species	Austrobaileyaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3158	Linum album	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3158	Linum album	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23682	Juniperus phoenicea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3158	Linum album	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11677	Lactobacillus acidophilus	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18173	Pyrocystis lunula	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3050	Cladonia pseudodidyma	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9535	Cortinarius basirubescens	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7807	Polyporus sulphureus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17709	Timonius kaniensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3746	Hesperocyparis nevadensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18847	Copaifera paupera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13594	Hippocratea indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21938	Coleus carnosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17718	Artemisia schmidtiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18575	Ochtodes crockeri	Species	Rhizophyllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12282	Parmelia conspersa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12072	Escallonia philippiana	Species	Escalloniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17068	Talaromyces wortmanni	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11603	Lathyrus macrorrhizus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10712	Tabebuia rosea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19189	Brickellia pendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15608	Tanacetum santolina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18520	Helipterum strictum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17275	Chamaemelum scariosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18061	Anacystis cyanea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17190	Senecio erraticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18242	Gleichenia glauca	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17596	Ficus maxima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18377	Chaetomium retardatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16829	Dunaliella acidophila	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19057	Lentinellus omphalodes	Species	Auriscalpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12801	Aglaia meridionalis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18792	Crotalaria lechnaultii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8247	Austrobaileya scandens	Species	Austrobaileyaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12785	Bursera fagaroides	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3158	Linum album	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23848	Podophyllum peltatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23682	Juniperus phoenicea	Species	Cupressaceae	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	3
ED50	1

Activity Type	# Activity
Cell line	1
Organism	2
Non-molecular	1

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
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.026	ug ml-1	PMID[6253598]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	23.0	nM	PMID[9834179]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	16.0	nM	PMID[27214307]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	IC50	=	23.0	nM	PMID[9834179]

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 NPC149505 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	28675
0.1-0.2	19780
0.2-0.3	1144
0.3-0.4	176
0.4-0.5	44
0.5-0.6	17
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC480477
0.7586	Intermediate Similarity	NPC80230
0.7586	Intermediate Similarity	NPC104024
0.7586	Intermediate Similarity	NPC101755
0.7586	Intermediate Similarity	NPC304687
0.7586	Intermediate Similarity	NPC65574
0.7458	Intermediate Similarity	NPC262455
0.7458	Intermediate Similarity	NPC177476
0.6892	Remote Similarity	NPC222531
0.6769	Remote Similarity	NPC115281
0.6308	Remote Similarity	NPC207584
0.6308	Remote Similarity	NPC19947
0.6061	Remote Similarity	NPC30009
0.6061	Remote Similarity	NPC103197
0.6032	Remote Similarity	NPC218092
0.6032	Remote Similarity	NPC239890
0.6032	Remote Similarity	NPC209411
0.6032	Remote Similarity	NPC246474
0.6032	Remote Similarity	NPC162851
0.5821	Remote Similarity	NPC210642
0.5821	Remote Similarity	NPC13985
0.5758	Remote Similarity	NPC237946
0.5758	Remote Similarity	NPC32373
0.5714	Remote Similarity	NPC163527
0.5652	Remote Similarity	NPC273578
0.5574	Remote Similarity	NPC40237
0.5556	Remote Similarity	NPC477698
0.55	Remote Similarity	NPC151423
0.541	Remote Similarity	NPC92693
0.5397	Remote Similarity	NPC164082
0.5375	Remote Similarity	NPC115624
0.5352	Remote Similarity	NPC288149
0.5352	Remote Similarity	NPC470637
0.5333	Remote Similarity	NPC218841
0.5211	Remote Similarity	NPC119910
0.5161	Remote Similarity	NPC475000

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC149505 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5502
0.1-0.2	3572
0.2-0.3	64
0.3-0.4	5
0.4-0.5	4
0.5-0.6	3
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
0.5758	Remote Similarity	NPD4965	Approved
0.5758	Remote Similarity	NPD4966	Phase 4
0.5758	Remote Similarity	NPD4967	Phase 2

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