NPASS Compound

Natural Product: NPC34963

Natural Product ID	NPC34963
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Shizukaol B
IUPAC Name	n.a.
Synonyms	Shizukaol B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1813267
PubChem CID	56661508
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 97105 0 0 0 0 0 0 0 0999 V2000 6.0016 0.1422 2.8491 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0573 0.5209 1.7951 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9043 -0.1932 0.6952 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6022 -1.4353 0.3210 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6531 -2.4864 0.1393 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9317 -3.7481 -0.2847 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1295 -4.0422 -0.5542 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 -4.7660 -0.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9874 -4.4295 -1.6541 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4239 -3.0740 -1.3125 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6412 -2.1207 -2.0958 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 -2.8500 -0.1862 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1286 -1.6603 0.2599 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0683 -1.0701 -0.5871 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2834 0.1477 -0.4771 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3203 1.1005 0.4571 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3970 2.4025 -0.2592 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0070 2.4086 -1.7100 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8077 1.5829 -2.6425 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1736 3.8806 -2.0025 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4406 4.4831 -2.4456 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2482 4.3899 -0.9750 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7095 3.0865 -0.3359 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4725 3.2156 0.9367 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3445 2.1048 0.9977 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2309 1.7507 1.9566 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3511 2.4527 2.9627 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5522 2.3992 -1.2240 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4191 1.9031 -1.7814 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3972 2.7724 -1.0920 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6912 2.4093 0.3251 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8813 1.1419 0.5456 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7837 0.1992 -0.6174 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9563 -1.1618 -0.0708 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4941 -2.1138 -0.7748 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9614 -1.9041 -2.1829 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8112 -3.4443 -0.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6319 -3.7377 0.9311 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3323 -4.4398 -1.0902 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6119 -5.7000 -0.5143 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4573 -1.4179 1.2773 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9364 -2.5228 1.5023 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 -0.4259 2.3823 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2158 0.7969 1.9049 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7363 0.5471 1.9793 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8901 2.0704 2.6589 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9968 3.1150 2.4612 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8166 3.1149 1.6026 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2669 -1.0068 3.4271 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4592 0.4663 -1.2955 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3704 -0.5114 -2.3107 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6366 -1.5719 -1.7940 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5603 -2.7357 -2.2325 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0395 0.4750 2.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7252 0.6762 3.7866 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0562 -0.9540 3.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1664 0.1459 -0.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3789 -1.7108 1.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1348 -1.3281 -0.6466 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2375 -4.8027 0.4775 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2976 -5.7926 -0.5507 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2389 -5.2081 -1.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -4.3950 -2.5671 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6554 -1.8881 1.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9321 -0.9193 0.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3227 0.8174 0.8487 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3503 1.2060 1.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3109 3.1313 0.2346 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3750 0.7966 -2.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1026 1.1701 -3.4415 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5282 2.1585 -3.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7269 4.4617 -2.1393 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3127 3.9586 -2.8253 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3726 5.5277 -2.8393 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9629 5.2468 -0.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0778 4.1182 1.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7616 3.1107 1.7883 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4068 2.8558 -1.3595 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6773 1.8470 -2.8783 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2042 3.8482 -1.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4149 2.6850 -1.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6033 0.5390 -1.2806 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0846 -0.8943 -2.5068 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9518 -2.4145 -2.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2484 -2.5229 -2.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6239 -6.0647 -0.8487 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8540 -6.4143 -0.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6851 -5.6454 0.5916 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5272 -0.2189 2.8346 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2234 1.0469 1.1029 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8930 -0.5391 1.8342 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1373 0.9277 2.9367 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2901 2.0723 3.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0450 3.8876 3.2575 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9824 2.7995 2.1005 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1135 3.9707 1.7139 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7326 -1.8030 3.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 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 0 26 27 2 0 23 28 1 6 18 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 34 41 1 0 41 42 2 0 41 43 1 0 43 44 1 0 44 45 1 6 44 46 1 0 46 47 1 0 47 48 1 0 43 49 1 0 33 50 1 0 50 51 1 6 51 52 1 0 52 53 2 0 26 2 1 0 50 29 1 0 52 14 1 0 50 15 1 0 23 17 1 0 48 31 1 0 22 20 1 0 44 32 1 0 48 46 1 0 1 54 1 0 1 55 1 0 1 56 1 0 3 57 1 0 4 58 1 0 4 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 13 64 1 0 13 65 1 0 16 66 1 0 16 67 1 0 17 68 1 1 19 69 1 0 19 70 1 0 19 71 1 0 20 72 1 1 21 73 1 0 21 74 1 0 22 75 1 1 24 76 1 0 24 77 1 0 28 78 1 0 29 79 1 6 30 80 1 0 30 81 1 0 33 82 1 6 36 83 1 0 36 84 1 0 36 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 43 89 1 1 45 90 1 0 45 91 1 0 45 92 1 0 46 93 1 1 47 94 1 0 47 95 1 0 48 96 1 1 49 97 1 0 M END

Standard InCHIKey	NCEFZVURTXZBJM-CLPLISGISA-N
Standard InCHI	InChI=1S/C40H44O13/c1-16-8-9-50-27(41)6-7-28(42)51-14-20-22-13-25-37(3,23-12-24(23)39(25,48)15-52-34(16)45)26-11-19-18-10-21(18)38(4)30(19)31(40(22,26)53-36(20)47)29(32(43)33(38)44)17(2)35(46)49-5/h8,18,21,23-26,31,33,44,48H,6-7,9-15H2,1-5H3/b16-8+,29-17-/t18-,21-,23-,24+,25-,26+,31+,33+,37+,38+,39+,40+/m1/s1
SMILES	C/C/1=CCOC(=O)CCC(=O)OCC2=C3C[C@@H]4[C@](C)([C@@H]5C[C@@H]5[C@]4(COC1=O)O)[C@@H]1CC4=C5[C@H](/C(=C(C)/C(=O)OC)/C(=O)[C@@H]([C@@]5(C)[C@@H]5C[C@H]45)O)[C@]31OC2=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	732.28	Volume:	711.296 ? Van der Waals volume.
Dense:	1.03	LogP:	1.149 ? 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:	-4.957 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	52.0
TPSA:	189.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	2.0	Rings:	9.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.173	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.997	Fsp³:	0.65
MCE-18:	218.182 ? 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:	0.628	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.84 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.294 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.173	Promiscuous compounds:	0.636

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.309	MDCK Permeability:	-4.912
Pgp-inhibitor:	0.003	Pgp-substrate:	0.288
PAMPA:	0.932 ? 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%):	0.913	30% Bioavailability (F30%):	0.64
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.304	MRP1:	1.0
Plasma Protein Binding (PPB):	67.9%	Volume Distribution (VD):	0.048
Fu:	30.584% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.001
BSEP inhibitor:	0.926

ADMET: Metabolism

CYP1A2-inhibitor:	0.011	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.018	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.999 ? 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):

3.665

Half-life (T1/2):

1.693

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.09
Human Hepatotoxicity (H-HT):	0.967	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.983	Rat Oral Acute Toxicity:	0.756
Maximum Recommended Daily Dose:	0.997	Skin Sensitization:	1.0
Carcinogencity:	0.997	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.041
Drug-induced Neurotoxicity:	0.661	Ototoxicity:	0.637
Hematotoxicity:	0.99	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.817
A549 Cytotoxicity:	0.878	Hek293 Cytotoxicity:	0.862
BCF:	0.408 ? 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:	3.623 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.724 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.859 ? 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
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1016/j.phytol.2016.01.005]
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]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18451544]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053511]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[19358604]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	Whole plant	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	whole plants	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21142110]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[21190690]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21650224]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21650224]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22372956]
NPO6674	Burkholderia ambifaria	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22988812]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[23394984]
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[2413754]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24216090]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588583]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27997206]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30673219]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724564]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[9542132]
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]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	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]
NPO3385	Cassine transvaalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9928	Cephalaria cilicica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8484	Codonopsis lanceolata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12192	Coronilla scorpioides	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]
NPO5827	Dalea tuberculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO468	Dryopteris oligophlebia	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9040	Elsinoe annonae	Species	Elsinoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7048	Eucalyptus rariflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6256	Eucalyptus umbra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9307	Ficus indica	Species	Ficidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5013	Loranthus spicatus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10399	Manfreda virginica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11815	Mikania hirsutissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12891	Minasia alpestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5392	Pachycereus pecten-aboriginum	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9512	Phlomis fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO936	Pinalia spicata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16164	Podocarpus urbani	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11555	Pterocaulon purpurascens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7345	Ptilonia magellanica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12998	Salvia rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1185	Stereocaulon strictum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19898	Stevia lucida	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]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO16164	Podocarpus urbani	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO936	Pinalia spicata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5013	Loranthus spicatus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5392	Pachycereus pecten-aboriginum	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6256	Eucalyptus umbra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3740	Trisetum flavescens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3385	Cassine transvaalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9512	Phlomis fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6674	Burkholderia ambifaria	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9928	Cephalaria cilicica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9040	Elsinoe annonae	Species	Elsinoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11815	Mikania hirsutissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10399	Manfreda virginica	Species	Asparagaceae	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]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	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
EC50	4
IC50	5
Activity	1
CC50	1

Activity Type	# Activity
Cell line	6
Organism	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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	150.0	nM	PMID[22372956]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	14790.0	nM	PMID[27177824]
NPT1374	Cell line	WI-38	Homo sapiens	IC50	=	16700.0	nM	PMID[27997206]
NPT113	Cell line	RAW264.7	Mus musculus	Activity	=	55.4	%	PMID[30724564]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[30724564]
NPT1452	Cell line	C8166	Homo sapiens	CC50	=	20.0	nM	PMID[21650224]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	27.0	nM	PMID[27997206]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	220.0	nM	PMID[21650224]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	470.0	nM	PMID[21650224]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	500.0	nM	PMID[21650224]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1.4	nM	PMID[21650224]

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 NPC34963 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	22698
0.1-0.2	26893
0.2-0.3	212
0.3-0.4	6
0.4-0.5	11
0.5-0.6	14
0.6-0.7	5
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC186637
0.8696	High Similarity	NPC290020
0.8409	Intermediate Similarity	NPC35109
0.8333	Intermediate Similarity	NPC58029
0.8152	Intermediate Similarity	NPC241935
0.8152	Intermediate Similarity	NPC486803
0.7979	Intermediate Similarity	NPC486797
0.7979	Intermediate Similarity	NPC164241
0.7979	Intermediate Similarity	NPC469673
0.7812	Intermediate Similarity	NPC486810
0.7802	Intermediate Similarity	NPC299570
0.7753	Intermediate Similarity	NPC15095
0.75	Intermediate Similarity	NPC486811
0.75	Intermediate Similarity	NPC220757
0.734	Intermediate Similarity	NPC196921
0.72	Intermediate Similarity	NPC279478
0.7172	Intermediate Similarity	NPC486798
0.7065	Intermediate Similarity	NPC275236
0.6947	Remote Similarity	NPC486799
0.6875	Remote Similarity	NPC59488
0.6804	Remote Similarity	NPC19772
0.6408	Remote Similarity	NPC213697
0.6	Remote Similarity	NPC486809
0.5648	Remote Similarity	NPC24599
0.5556	Remote Similarity	NPC192334
0.5556	Remote Similarity	NPC60150
0.551	Remote Similarity	NPC263046
0.5364	Remote Similarity	NPC470427
0.5364	Remote Similarity	NPC486808
0.5347	Remote Similarity	NPC17938
0.5263	Remote Similarity	NPC309497
0.5263	Remote Similarity	NPC611150
0.5234	Remote Similarity	NPC469381
0.5225	Remote Similarity	NPC327664
0.5225	Remote Similarity	NPC481183
0.5225	Remote Similarity	NPC476097
0.5044	Remote Similarity	NPC470426

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC34963 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7344
0.1-0.2	1786
0.2-0.3	20
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