NPASS Compound

Natural Product: NPC94509

Natural Product ID	NPC94509
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MOPJOSMHIBNYOK-OFEMSGAVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2448519
PubChem CID	70692363
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

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 76 79 0 0 0 0 0 0 0 0999 V2000 7.2061 1.7688 0.8586 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7248 1.7927 0.8937 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0077 1.0144 0.0834 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5629 1.0221 0.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8480 1.7290 0.8418 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8885 0.1684 -0.7861 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5001 0.1180 -0.8290 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9872 -1.2303 -0.9244 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5641 -1.2755 -0.9234 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5888 -2.7549 -1.2384 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3874 -3.3389 -0.4766 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2648 -2.3150 -0.0109 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8481 -2.0770 1.4192 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6864 -2.0473 1.4016 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0716 -0.9446 0.4593 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5065 -0.5502 0.4502 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4118 -1.5827 -0.1706 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0211 -0.3524 1.8529 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3946 0.6543 2.6717 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1560 0.7227 2.8234 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0980 1.6639 3.3793 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5338 0.7946 -0.2929 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8658 0.7794 -1.6006 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0613 -0.4101 -1.9994 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0492 0.1058 -2.7790 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0995 0.7437 -2.1473 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6428 1.7371 -2.6429 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8405 1.4848 -0.2591 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0344 0.8543 -0.8527 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7243 2.8528 -0.7985 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6281 3.3113 -1.1325 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8258 3.6963 -0.9598 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6612 5.0023 -1.4867 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1131 -3.3175 1.0178 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2863 -0.8828 1.9207 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6564 -2.8493 -0.0715 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6389 -2.1735 0.2822 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9149 -4.1364 -0.5312 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2432 -4.6170 -0.5829 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0136 2.6742 1.8328 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5133 2.0200 -0.1933 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5955 2.5942 1.4944 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6249 0.7828 1.1330 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5403 0.3629 -0.5999 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0792 0.8125 -0.0750 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2311 -1.6114 -1.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5527 -3.2252 -1.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2025 -2.8160 -2.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2260 -2.8807 2.0516 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9874 -1.9216 2.4391 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4964 -0.0542 0.7900 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4411 -1.3899 0.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1532 -2.5543 0.3431 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3639 -1.6604 -1.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9231 -1.3529 2.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1316 -0.1928 1.8648 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7784 2.6460 3.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8725 1.4215 0.4016 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6098 0.9610 -2.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2145 1.7100 -1.6745 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6080 -1.0425 -2.7333 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1012 1.6685 0.8407 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9084 0.0691 -1.5884 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6661 1.6363 -1.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7610 0.4962 -0.0853 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6585 5.3887 -1.2940 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7976 4.9982 -2.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4256 5.6582 -1.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4954 -3.8528 1.7589 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9651 -0.9367 2.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5020 -4.9514 0.4608 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3252 -5.5092 -1.2525 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9829 -3.8412 -0.8890 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4201 3.3922 1.2617 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7645 3.2549 2.4346 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3953 2.0845 2.5610 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 16 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 22 28 1 0 28 29 1 0 28 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 14 34 1 0 13 35 1 0 12 36 1 1 36 37 2 0 36 38 1 0 38 39 1 0 2 40 1 0 26 7 1 0 12 8 1 0 24 9 1 0 15 9 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 0 7 45 1 1 8 46 1 6 10 47 1 0 10 48 1 0 13 49 1 1 14 50 1 1 15 51 1 1 17 52 1 0 17 53 1 0 17 54 1 0 18 55 1 0 18 56 1 0 21 57 1 0 22 58 1 1 23 59 1 0 23 60 1 0 24 61 1 6 28 62 1 1 29 63 1 0 29 64 1 0 29 65 1 0 33 66 1 0 33 67 1 0 33 68 1 0 34 69 1 0 35 70 1 0 39 71 1 0 39 72 1 0 39 73 1 0 40 74 1 0 40 75 1 0 40 76 1 0 M END

Standard InCHIKey	MOPJOSMHIBNYOK-OFEMSGAVSA-N
Standard InCHI	InChI=1S/C27H36O13/c1-11(2)7-16(30)40-18-20-26-10-38-27(20,24(35)37-6)21(32)17(31)19(26)25(4,9-15(28)29)13(12(3)22(33)36-5)8-14(26)39-23(18)34/h7,12-14,17-21,31-32H,8-10H2,1-6H3,(H,28,29)/t12-,13-,14+,17+,18+,19+,20+,21-,25-,26+,27-/m0/s1
SMILES	CC(=CC(=O)O[C@@H]1[C@@H]2[C@]34CO[C@@]2([C@H]([C@@H]([C@@H]4[C@@](C)(CC(=O)O)[C@@H](C[C@H]3OC1=O)[C@H](C)C(=O)OC)O)O)C(=O)OC)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.22	Volume:	539.776 ? Van der Waals volume.
Dense:	1.053	LogP:	1.007 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.561 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.303 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	24.0
TPSA:	192.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.211	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.55	Fsp³:	0.741
MCE-18:	122.872 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.346	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.08	Promiscuous compounds:	0.395

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.752	MDCK Permeability:	-5.177
Pgp-inhibitor:	0.0	Pgp-substrate:	0.392
PAMPA:	0.988 ? 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):	0.001
20% Bioavailability (F20%):	0.017	30% Bioavailability (F30%):	0.049
50% Bioavailability (F50%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	1.0
Plasma Protein Binding (PPB):	56.775%	Volume Distribution (VD):	-0.496
Fu:	43.366% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.001
BSEP inhibitor:	0.026

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.297	CYP3A4-substrate:	0.497
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
HLM stability:	0.003 ? 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):

2.156

Half-life (T1/2):

2.537

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.692	Drug-induced Liver Injury (DILI):	0.982
AMES Toxicity:	0.656	Rat Oral Acute Toxicity:	0.35
Maximum Recommended Daily Dose:	0.293	Skin Sensitization:	1.0
Carcinogencity:	0.195	Eye Corrosion:	0.008
Eye Irritation:	0.451	Respiratory Toxicity:	0.164
Drug-induced Neurotoxicity:	0.599	Ototoxicity:	0.687
Hematotoxicity:	0.485	Drug-induced Nephrotoxicity:	0.993
Genotoxicity:	0.957	RPMI-8226 Immunitoxicity:	0.12
A549 Cytotoxicity:	0.007	Hek293 Cytotoxicity:	0.098
BCF:	0.232 ? 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:	2.947 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.471 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.621 ? 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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15949825]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18723353]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26522747]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29873264]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33172599]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36253818]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350091]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14150	Solanum jamaicense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12944	Sideritis tragoriganum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11637	Psilostrophe cooperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14528	Pneumatospora obcoronata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12717	Parmelia metastrigosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11873	Oecophylla smaragdina	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14749	Lippia carviodora	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1641	Amycolatopsis azurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26718	Chelidonura fulvipunctata	Species	Aglajidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14845	Ceratophyllum submersum	Species	Ceratophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9203	Cephalonomia gallicola	Species	Bethylidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11432	Centrolobium tomentosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5303	Castanea crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10818	Carpobrotus edulis	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11084	Asplenium normale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3164	Yponomeuta malinellus	Species	Yponomeutidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14749	Lippia carviodora	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11637	Psilostrophe cooperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5303	Castanea crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14528	Pneumatospora obcoronata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14845	Ceratophyllum submersum	Species	Ceratophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1641	Amycolatopsis azurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11873	Oecophylla smaragdina	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11432	Centrolobium tomentosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12717	Parmelia metastrigosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9203	Cephalonomia gallicola	Species	Bethylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26718	Chelidonura fulvipunctata	Species	Aglajidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11084	Asplenium normale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14150	Solanum jamaicense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12944	Sideritis tragoriganum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3164	Yponomeuta malinellus	Species	Yponomeutidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10818	Carpobrotus edulis	Species	Aizoaceae	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	5

Activity Type	# Activity
Cell line	5

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
NPT180	Cell line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[22506620]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[22506620]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[22506620]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[22506620]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[22506620]

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 NPC94509 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	15042
0.1-0.2	32937
0.2-0.3	1810
0.3-0.4	18
0.4-0.5	14
0.5-0.6	28
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8133	Intermediate Similarity	NPC190185
0.7922	Intermediate Similarity	NPC479017
0.65	Remote Similarity	NPC89929
0.65	Remote Similarity	NPC479018
0.6341	Remote Similarity	NPC146432
0.6341	Remote Similarity	NPC470778
0.6329	Remote Similarity	NPC213084
0.5952	Remote Similarity	NPC476008
0.593	Remote Similarity	NPC480785
0.593	Remote Similarity	NPC480787
0.593	Remote Similarity	NPC480784
0.5882	Remote Similarity	NPC18945
0.5882	Remote Similarity	NPC152301
0.5698	Remote Similarity	NPC480783
0.5667	Remote Similarity	NPC480786
0.5667	Remote Similarity	NPC470779
0.5581	Remote Similarity	NPC24651
0.5568	Remote Similarity	NPC67251
0.5521	Remote Similarity	NPC190065
0.5506	Remote Similarity	NPC265557
0.5444	Remote Similarity	NPC476729
0.5385	Remote Similarity	NPC480777
0.5357	Remote Similarity	NPC470776
0.5357	Remote Similarity	NPC17772
0.53	Remote Similarity	NPC480779
0.5287	Remote Similarity	NPC299849
0.5269	Remote Similarity	NPC105926
0.5253	Remote Similarity	NPC141215
0.5253	Remote Similarity	NPC262813
0.52	Remote Similarity	NPC479019
0.5172	Remote Similarity	NPC485623
0.5149	Remote Similarity	NPC295885
0.5116	Remote Similarity	NPC143268
0.5098	Remote Similarity	NPC140045
0.5096	Remote Similarity	NPC480778

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC94509 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5098
0.1-0.2	3997
0.2-0.3	55
0.3-0.4	0
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