NPASS Compound

Natural Product: NPC248029

Natural Product ID	NPC248029
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OGJKMZVUJJYWKO-CYBMUJFWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	193686
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002660] Proaporphines

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 41 44 0 0 0 0 0 0 0 0999 V2000 4.5715 -0.8752 0.4786 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2783 -1.4130 0.3812 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1821 -0.5816 0.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3868 0.7804 0.3533 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2953 1.6370 0.2905 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4605 3.1071 0.3489 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1335 3.7711 0.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9460 3.0563 0.8438 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1958 1.8517 0.0989 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1664 0.8889 0.6808 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6632 -0.4689 0.0816 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1705 -0.4903 -1.2738 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0423 -1.3884 -1.6721 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5635 -2.4249 -0.7897 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3992 -3.2888 -1.1649 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0417 -2.3923 0.5807 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1778 -1.4893 0.9462 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1886 -0.2867 0.1591 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0684 1.0718 0.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9026 -1.1023 0.2222 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7439 -2.4657 0.1909 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7535 -3.1088 -1.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8172 -0.3152 -0.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3229 -1.6718 0.6358 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6622 -0.1629 1.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3590 1.2473 0.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8953 3.3935 1.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1880 3.4734 -0.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1116 3.7126 -0.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1772 4.8285 0.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5663 2.7753 1.7716 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3584 2.0592 -0.9728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 1.0738 0.3406 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1092 0.8415 1.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8396 0.2550 -2.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4291 -1.4049 -2.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4134 -3.1619 1.2780 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8292 -1.5233 1.9869 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3182 -3.2748 -1.3659 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2260 -2.4684 -1.8545 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3081 -4.0653 -1.0202 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 11 18 1 0 18 19 1 0 18 20 2 0 20 21 1 0 21 22 1 0 20 3 1 0 19 5 2 0 19 9 1 0 17 11 1 0 1 23 1 0 1 24 1 0 1 25 1 0 4 26 1 0 6 27 1 0 6 28 1 0 7 29 1 0 7 30 1 0 8 31 1 0 9 32 1 6 10 33 1 0 10 34 1 0 12 35 1 0 13 36 1 0 16 37 1 0 17 38 1 0 22 39 1 0 22 40 1 0 22 41 1 0 M END

Standard InCHIKey	OGJKMZVUJJYWKO-CYBMUJFWSA-N
Standard InCHI	InChI=1S/C18H19NO3/c1-21-14-9-11-5-8-19-13-10-18(6-3-12(20)4-7-18)16(15(11)13)17(14)22-2/h3-4,6-7,9,13,19H,5,8,10H2,1-2H3/t13-/m1/s1
SMILES	COc1cc2CCN[C@@H]3CC4(C=CC(=O)C=C4)c(c23)c1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	297.14	Volume:	307.207 ? Van der Waals volume.
Dense:	0.967	LogP:	1.85 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.991 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.507 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	21.0
TPSA:	47.56 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.909	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.041	Fsp³:	0.389
MCE-18:	96.8 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.702	Fluc inhibitor:	0.113 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.8 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.226 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.006	Promiscuous compounds:	0.339

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.969	MDCK Permeability:	-4.757
Pgp-inhibitor:	0.052	Pgp-substrate:	0.988
PAMPA:	0.052 ? 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):	0.005
20% Bioavailability (F20%):	0.016	30% Bioavailability (F30%):	0.384
50% Bioavailability (F50%):	0.828

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.791	MRP1:	0.806
Plasma Protein Binding (PPB):	67.036%	Volume Distribution (VD):	0.184
Fu:	30.543% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.135
OATP1B3 inhibitor:	0.199	BCRP inhibitor:	0.035
BSEP inhibitor:	0.946

ADMET: Metabolism

CYP1A2-inhibitor:	0.891	CYP1A2-substrate:	0.399
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.108	CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.727	CYP3A4-substrate:	0.417
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	0.945
HLM stability:	0.98 ? 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):

8.387

Half-life (T1/2):

1.839

ADMET: Toxicity

hERG Blockers:	0.135	hERG Blockers (10um):	0.434
Human Hepatotoxicity (H-HT):	0.594	Drug-induced Liver Injury (DILI):	0.421
AMES Toxicity:	0.543	Rat Oral Acute Toxicity:	0.606
Maximum Recommended Daily Dose:	0.601	Skin Sensitization:	0.579
Carcinogencity:	0.582	Eye Corrosion:	0.249
Eye Irritation:	0.89	Respiratory Toxicity:	0.806
Drug-induced Neurotoxicity:	0.742	Ototoxicity:	0.318
Hematotoxicity:	0.385	Drug-induced Nephrotoxicity:	0.459
Genotoxicity:	0.419	RPMI-8226 Immunitoxicity:	0.088
A549 Cytotoxicity:	0.052	Hek293 Cytotoxicity:	0.244
BCF:	1.512 ? 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:	4.125 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.377 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.818 ? 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
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(88)80746-5]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94986-0]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3987/COM-96-7609.]
NPO25388	Siliquariaspongia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10425118]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575964]
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858757]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO21740	Ajuga salicifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713393]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038566]
NPO27931	Caulerpa taxifolia	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16563751]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[16964757]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	root bark	Buea, Southwest Province, Cameroon	1997-JUL	PMID[17125223]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	flower	n.a.	PMID[17679444]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18081254]
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18980381]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[20030508]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[20645211]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23059629]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23132311]
NPO31236	Stephania dentifolia	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[23713286]
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	aerial parts	Alpa Corral, Cordoba, Argentina	2008-Aug	PMID[25517209]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25832441]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27617953]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28257196]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36325999]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3728032]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759160]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9428163]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27468	Rhizopogon roseolus	Species	Rhizopogonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27976	Astragalus wootoni	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27869	Bombacopsis glabra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27931	Caulerpa taxifolia	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27726	Diplocarpon mali	Species	Dermateaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27703	Eclipta erecta	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27522	Gongronella urceolifera	Species	Cunninghamellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18354	Meiothermus ruber	Species	Thermaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27216	Oreodaphne porosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26332	Ramalina tumidula	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27838	Rebutia marsoneri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25388	Siliquariaspongia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14677	Brachylaena neriifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24050	Stephania glabra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24183	Brickellia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21740	Ajuga salicifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5902	Stephania bancroftii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22514	Cetraria cucullata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23885	Agathosma bisulca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13528	Funneliformis mosseae	Species	Glomeraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1327	Heliothis maritima	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22738	Horsfieldia iryaghedhi	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24365	Hymenoxys ivesiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23414	Karwinskia subcordata	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23550	Maytenus octogona	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23461	Medicago hispida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19027	Passiflora coccinea	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23282	Russula paludosa	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24050	Stephania glabra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24050	Stephania glabra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24050	Stephania glabra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27976	Astragalus wootoni	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27726	Diplocarpon mali	Species	Dermateaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24183	Brickellia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22738	Horsfieldia iryaghedhi	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23282	Russula paludosa	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27703	Eclipta erecta	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27838	Rebutia marsoneri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27468	Rhizopogon roseolus	Species	Rhizopogonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27216	Oreodaphne porosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25388	Siliquariaspongia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18354	Meiothermus ruber	Species	Thermaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26332	Ramalina tumidula	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19027	Passiflora coccinea	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27869	Bombacopsis glabra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27522	Gongronella urceolifera	Species	Cunninghamellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23885	Agathosma bisulca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1327	Heliothis maritima	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27931	Caulerpa taxifolia	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23461	Medicago hispida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14677	Brachylaena neriifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21740	Ajuga salicifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24050	Stephania glabra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22514	Cetraria cucullata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5902	Stephania bancroftii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22390	Virola theiodora	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23550	Maytenus octogona	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23414	Karwinskia subcordata	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20961	Hugonia oreogena	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24365	Hymenoxys ivesiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13528	Funneliformis mosseae	Species	Glomeraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC248029 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	26224
0.1-0.2	22824
0.2-0.3	749
0.3-0.4	56
0.4-0.5	4
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	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC2770
1.0	High Similarity	NPC39103

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC248029 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4641
0.1-0.2	4414
0.2-0.3	93
0.3-0.4	2
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