NPASS Compound

Natural Product: NPC63186

Natural Product ID	NPC63186
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CUGZBEHTWRBHKV-AOSINFTKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3809663
PubChem CID	54671620
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 73 80 0 0 0 0 0 0 0 0999 V2000 2.5483 -0.9317 -5.4510 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2070 -0.6551 -4.1099 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8907 -1.5347 -3.1404 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9104 -2.7890 -3.4773 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5284 -1.2154 -1.7710 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4893 -0.0449 -1.2431 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9090 1.1298 -2.0472 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6901 1.0283 -2.9461 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3167 2.4847 -1.6797 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9180 3.4930 -2.3799 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5171 2.5608 -0.2071 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0375 1.4205 0.5556 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9989 0.1182 0.1251 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3277 -0.7853 0.9464 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1331 -0.8182 2.0689 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1871 -1.9699 2.7408 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8591 -2.3143 3.7844 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2710 -2.8437 2.0289 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1767 -2.1067 1.0470 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3498 -2.5075 0.1383 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8631 -1.2735 -0.4961 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1440 -0.2950 0.6388 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9646 0.0036 1.5006 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7889 1.2641 2.1133 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5814 1.8524 1.8612 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4089 1.5539 2.9205 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8652 2.0085 4.0357 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4019 3.3791 1.7330 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0924 3.7871 0.4784 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7018 4.1564 1.7940 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2464 -0.9868 1.4662 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8045 0.8184 -0.0707 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3402 0.8230 -0.1616 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6177 0.0839 -1.1899 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2441 -1.3489 -1.0467 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9522 -2.4244 -1.3645 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0626 -4.2651 2.3676 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0706 2.4850 -0.0373 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6289 -2.3416 -0.7731 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4729 -1.4582 -5.6207 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6895 -1.4518 -5.9756 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6478 0.0657 -5.9752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2546 2.4314 -1.9045 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3881 3.2169 -3.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0153 -3.2314 -0.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1629 -2.9762 0.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2617 -0.8285 -1.2903 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2441 -0.6526 2.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5824 2.0362 1.8547 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8826 1.2384 3.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4862 2.7208 4.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5378 3.8343 2.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7481 4.6402 -0.1373 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6510 3.6339 2.0212 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6911 5.1997 2.0976 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6847 -0.2173 2.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7010 -1.6758 2.1560 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9733 -1.5187 0.8715 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2695 1.7045 -0.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7596 1.7938 -0.4129 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9097 0.3089 0.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5464 0.5335 -2.2052 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9527 -2.3996 -1.7562 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4701 -3.3843 -1.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8495 -4.9103 2.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3962 -4.2760 3.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8843 -4.6178 1.7495 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3145 2.0012 0.9288 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5280 3.4636 -0.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4770 1.8229 -0.8398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2063 -3.2731 -0.9474 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6833 -2.7164 -1.2597 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2109 -2.0569 0.1360 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 3 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 1 15 16 1 0 16 17 2 0 16 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 1 0 25 26 1 1 26 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 22 31 1 1 22 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 18 37 1 0 11 38 1 6 5 39 1 0 13 6 1 0 19 14 1 0 35 21 1 0 29 11 1 0 34 32 1 0 25 12 1 0 30 28 1 0 23 14 1 0 1 40 1 0 1 41 1 0 1 42 1 0 9 43 1 1 10 44 1 0 20 45 1 0 20 46 1 0 21 47 1 6 23 48 1 1 24 49 1 0 24 50 1 0 27 51 1 0 28 52 1 6 29 53 1 6 30 54 1 0 30 55 1 0 31 56 1 0 31 57 1 0 31 58 1 0 32 59 1 6 33 60 1 0 33 61 1 0 34 62 1 6 36 63 1 0 36 64 1 0 37 65 1 0 37 66 1 0 37 67 1 0 38 68 1 0 38 69 1 0 38 70 1 0 39 71 1 0 39 72 1 0 39 73 1 0 M END

Standard InCHIKey	CUGZBEHTWRBHKV-AOSINFTKSA-N
Standard InCHI	InChI=1S/C31H34O8/c1-11-14-7-17(14)28(4)15(11)8-16-12(2)27(35)38-31(16)20(28)10-30(39-36)19-9-18(19)29(5)24(30)22(31)21(23(32)25(29)33)13(3)26(34)37-6/h14-15,17-20,25,33,36H,1,7-10H2,2-6H3/b21-13-/t14-,15+,17-,18-,19+,20+,25+,28-,29+,30+,31+/m1/s1
SMILES	COC(=O)/C(=C/1C(=O)[C@H](O)[C@@]2(C3=C1[C@]14OC(=O)C(=C1C[C@@H]1[C@]([C@@H]4C[C@]3(OO)[C@@H]3[C@H]2C3)(C)[C@@H]2C[C@@H]2C1=C)C)C)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.23	Volume:	528.147 ? Van der Waals volume.
Dense:	1.012	LogP:	1.596 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.969 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.03 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	36.0
TPSA:	119.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	2.0	Rings:	8.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.182	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.684	Fsp³:	0.645
MCE-18:	190.176 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.755	Fluc inhibitor:	0.055 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.564 ? 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:	0.268	Promiscuous compounds:	0.618

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152	MDCK Permeability:	-4.797
Pgp-inhibitor:	0.011	Pgp-substrate:	0.253
PAMPA:	0.856 ? 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%):	0.436	30% Bioavailability (F30%):	0.728
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.928	MRP1:	0.988
Plasma Protein Binding (PPB):	93.78%	Volume Distribution (VD):	0.276
Fu:	6.7% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.665
BSEP inhibitor:	0.891

ADMET: Metabolism

CYP1A2-inhibitor:	0.32	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.993
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.451 ? 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):

6.162

Half-life (T1/2):

1.758

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.155
Human Hepatotoxicity (H-HT):	0.899	Drug-induced Liver Injury (DILI):	0.748
AMES Toxicity:	0.842	Rat Oral Acute Toxicity:	0.743
Maximum Recommended Daily Dose:	0.704	Skin Sensitization:	0.999
Carcinogencity:	0.716	Eye Corrosion:	0.0
Eye Irritation:	0.082	Respiratory Toxicity:	0.432
Drug-induced Neurotoxicity:	0.195	Ototoxicity:	0.743
Hematotoxicity:	0.856	Drug-induced Nephrotoxicity:	0.895
Genotoxicity:	0.989	RPMI-8226 Immunitoxicity:	0.162
A549 Cytotoxicity:	0.374	Hek293 Cytotoxicity:	0.356
BCF:	1.431 ? 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:	4.292 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.32 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.54 ? 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
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	Spanish		DOI[10.1021/jf00010a019]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		DOI[10.1021/jf00016a013]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	Germany		DOI[10.1021/jf00016a013]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	Italy		DOI[10.1021/jf00016a013]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	Turkey		DOI[10.1111/j.1745-4557.2003.tb00250.x]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		DOI[10.17660/ActaHortic.2003.610.16]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[10794642]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[10820090]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[11754554]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[15315387]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[16076125]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[16920856]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[19358604]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[21190690]
NPO6674	Burkholderia ambifaria	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22988812]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	Germany		PMID[23394984]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	New Zealand		PMID[23394984]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[23394984]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[2413754]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24216090]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30673219]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[9542132]
NPO3385	Cassine transvaalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6674	Burkholderia ambifaria	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10399	Manfreda virginica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19898	Stevia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1185	Stereocaulon strictum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12998	Salvia rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7345	Ptilonia magellanica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11555	Pterocaulon purpurascens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16164	Podocarpus urbani	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO936	Pinalia spicata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9512	Phlomis fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5392	Pachycereus pecten-aboriginum	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12891	Minasia alpestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11815	Mikania hirsutissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3740	Trisetum flavescens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5013	Loranthus spicatus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9307	Ficus indica	Species	Ficidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6256	Eucalyptus umbra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7048	Eucalyptus rariflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9040	Elsinoe annonae	Species	Elsinoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO468	Dryopteris oligophlebia	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5827	Dalea tuberculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10738	Cotoneaster horizontalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12192	Coronilla scorpioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8484	Codonopsis lanceolata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9928	Cephalaria cilicica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10399	Manfreda virginica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16164	Podocarpus urbani	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11815	Mikania hirsutissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9040	Elsinoe annonae	Species	Elsinoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9928	Cephalaria cilicica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6674	Burkholderia ambifaria	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9512	Phlomis fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3385	Cassine transvaalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3740	Trisetum flavescens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6256	Eucalyptus umbra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5392	Pachycereus pecten-aboriginum	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5013	Loranthus spicatus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO936	Pinalia spicata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7048	Eucalyptus rariflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9307	Ficus indica	Species	Ficidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5827	Dalea tuberculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10738	Cotoneaster horizontalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11555	Pterocaulon purpurascens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12891	Minasia alpestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1185	Stereocaulon strictum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO468	Dryopteris oligophlebia	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19898	Stevia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12998	Salvia rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12192	Coronilla scorpioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7345	Ptilonia magellanica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8484	Codonopsis lanceolata	Species	Campanulaceae	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
Inhibition	1

Activity Type	# Activity
Cell line	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
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	<	50.0	%	PMID[27177824]

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 NPC63186 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	18527
0.1-0.2	30998
0.2-0.3	301
0.3-0.4	23
0.4-0.5	3
0.5-0.6	5
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	Natural Product ID
0.7125	Intermediate Similarity	NPC486802
0.55	Remote Similarity	NPC100347
0.5392	Remote Similarity	NPC486801
0.5243	Remote Similarity	NPC486800
0.5238	Remote Similarity	NPC309497
0.5238	Remote Similarity	NPC611150

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC63186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7018
0.1-0.2	2109
0.2-0.3	23
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