NPASS Compound

Natural Product: NPC36744

Natural Product ID	NPC36744
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FWNZEKQVBDXWKA-NJFOSAQPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11968746
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 98102 0 0 0 0 0 0 0 0999 V2000 9.1011 1.0273 -0.3786 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6480 -0.2797 0.2277 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8011 -1.2758 0.0265 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4898 -0.8458 -0.5099 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0404 -2.1470 0.0984 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2597 0.0843 -0.5249 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7892 0.3655 0.8380 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6316 1.2446 1.0868 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7831 2.6358 0.4952 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2870 0.7407 1.3134 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4056 2.0060 1.5658 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4109 2.0586 0.4594 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5885 0.8342 -0.3656 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3394 0.1645 -0.8108 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4072 1.0255 -1.7732 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7518 0.4385 -2.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3327 -0.4819 -1.2700 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6931 -0.9472 -1.6819 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5726 -0.9141 -0.4759 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9619 -1.8529 0.5421 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6830 -1.2144 1.0421 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6707 -1.0409 -0.0694 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1798 -2.4171 -0.4311 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5989 -0.0949 0.3483 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1689 -0.4291 1.5658 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5387 -0.9438 1.3987 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4672 -0.1104 0.4956 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9975 -1.0939 -0.4654 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8783 -1.2956 -0.7146 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7038 -0.2900 -0.2798 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6215 0.2729 -1.3342 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1228 1.5996 -0.8019 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1738 1.5852 0.6894 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2803 0.2379 1.3184 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7214 -0.2426 1.4104 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8016 -1.3750 2.2171 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4889 -0.7425 0.7792 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1468 2.3360 1.2786 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3028 1.9961 -1.3980 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9760 0.4016 -2.5623 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2140 1.1442 -0.2426 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9159 1.0284 -1.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6209 1.8674 0.1477 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5418 -0.1950 1.3121 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8340 -1.6289 -1.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7573 -0.8597 0.4064 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5369 -2.1577 0.6636 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7876 -1.0390 -1.5569 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9438 -2.0771 1.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7723 -2.9730 -0.1057 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0672 -2.4925 -0.3041 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5448 -0.4816 -1.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4891 0.9904 -1.1322 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5614 -0.6021 1.3977 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7243 0.6917 1.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8913 1.5824 2.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9624 2.9314 -0.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7703 2.6024 -0.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9246 3.4352 1.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3038 0.2674 2.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0217 2.9073 1.6600 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8600 1.9241 2.5263 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5843 3.0194 -0.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3612 2.2057 0.8510 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1761 1.1124 -1.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6204 -0.7610 -1.3562 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5784 2.0598 -1.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1300 1.1075 -2.7352 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2892 0.8294 -2.9151 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6311 -1.9969 -2.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0683 -0.3302 -2.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5140 0.1050 0.0008 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7362 -2.8523 0.1352 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6317 -1.9665 1.4185 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9121 -0.2594 1.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3148 -1.9032 1.8417 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1134 -2.5073 -0.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7061 -2.8349 -1.3368 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4155 -3.1607 0.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1312 0.8868 0.5361 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0736 0.3714 2.3621 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3954 -1.2863 2.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0283 -0.9421 2.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5056 -2.0107 1.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1792 -1.8436 -0.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8136 -1.7395 -0.0636 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2240 -0.7101 -1.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1183 0.5753 0.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4917 -0.3961 -1.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3301 2.3501 -1.0944 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1151 2.1419 0.9800 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9525 0.3570 2.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3517 0.5367 1.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1495 -0.3771 0.4122 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2831 -2.0609 1.6698 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7420 1.8806 2.0569 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3968 2.9925 -1.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0513 -0.4783 -3.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 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 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 19 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 32 39 1 0 31 40 1 0 27 10 1 0 37 30 1 0 27 13 1 0 24 14 1 0 22 17 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 5 49 1 0 5 50 1 0 5 51 1 0 6 52 1 0 6 53 1 0 7 54 1 0 7 55 1 0 8 56 1 0 9 57 1 0 9 58 1 0 9 59 1 0 10 60 1 0 11 61 1 0 11 62 1 0 12 63 1 0 12 64 1 0 13 65 1 0 14 66 1 0 15 67 1 0 15 68 1 0 16 69 1 0 18 70 1 0 18 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 21 75 1 0 21 76 1 0 23 77 1 0 23 78 1 0 23 79 1 0 24 80 1 0 25 81 1 0 25 82 1 0 26 83 1 0 26 84 1 0 28 85 1 0 28 86 1 0 28 87 1 0 30 88 1 1 31 89 1 6 32 90 1 1 33 91 1 6 34 92 1 1 35 93 1 0 35 94 1 0 36 95 1 0 38 96 1 0 39 97 1 0 40 98 1 0 M END

Standard InCHIKey	FWNZEKQVBDXWKA-NJFOSAQPSA-N
Standard InCHI	InChI=1S/C34H58O6/c1-19(2)20(3)7-8-21(4)25-11-12-26-24-10-9-22-17-23(13-15-33(22,5)27(24)14-16-34(25,26)6)39-32-31(38)30(37)29(36)28(18-35)40-32/h9,19-21,23-32,35-38H,7-8,10-18H2,1-6H3/t20?,21?,23?,24?,25?,26?,27?,28-,29-,30+,31-,32-,33?,34?/m1/s1
SMILES	CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.42	Volume:	603.943 ? Van der Waals volume.
Dense:	0.931	LogP:	5.026 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.827 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.891 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	26.0
TPSA:	99.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.293	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.951	Fsp³:	0.941
MCE-18:	91.212 ? 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:	0.982	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.028 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.207	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212	MDCK Permeability:	-5.047
Pgp-inhibitor:	0.001	Pgp-substrate:	0.022
PAMPA:	0.199 ? 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%):	0.0	30% Bioavailability (F30%):	0.053
50% Bioavailability (F50%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994	MRP1:	0.979
Plasma Protein Binding (PPB):	87.339%	Volume Distribution (VD):	-0.324
Fu:	12.378% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.023
OATP1B3 inhibitor:	0.971	BCRP inhibitor:	0.008
BSEP inhibitor:	0.04

ADMET: Metabolism

CYP1A2-inhibitor:	0.055	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.462
CYP2C9-inhibitor:	0.364	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.991	CYP2C8-inhibitor:	1.0
HLM stability:	0.985 ? 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):

4.539

Half-life (T1/2):

1.43

ADMET: Toxicity

hERG Blockers:	0.203	hERG Blockers (10um):	0.444
Human Hepatotoxicity (H-HT):	0.823	Drug-induced Liver Injury (DILI):	0.307
AMES Toxicity:	0.301	Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.446	Skin Sensitization:	0.902
Carcinogencity:	0.142	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.086
Drug-induced Neurotoxicity:	0.021	Ototoxicity:	0.993
Hematotoxicity:	0.222	Drug-induced Nephrotoxicity:	0.236
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.114
A549 Cytotoxicity:	0.777	Hek293 Cytotoxicity:	0.605
BCF:	3.138 ? 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:	5.408 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.064 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.35 ? 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
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11356-018-3422-z]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO8133	Woodwardia orientalis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8133	Woodwardia orientalis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8133	Woodwardia orientalis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8133	Woodwardia orientalis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8133	Woodwardia orientalis	Species	Blechnaceae	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 NPC36744 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	19571
0.1-0.2	23070
0.2-0.3	5724
0.3-0.4	1257
0.4-0.5	164
0.5-0.6	50
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9206	High Similarity	NPC22140
0.9206	High Similarity	NPC243728
0.806	Intermediate Similarity	NPC158088
0.7826	Intermediate Similarity	NPC282669
0.7333	Intermediate Similarity	NPC486114
0.7	Intermediate Similarity	NPC473890
0.6944	Remote Similarity	NPC470434
0.6625	Remote Similarity	NPC272015
0.6625	Remote Similarity	NPC295389
0.6622	Remote Similarity	NPC608180
0.6571	Remote Similarity	NPC207617
0.6571	Remote Similarity	NPC607440
0.6456	Remote Similarity	NPC296686
0.6296	Remote Similarity	NPC181845
0.5921	Remote Similarity	NPC21064
0.5797	Remote Similarity	NPC44083
0.5732	Remote Similarity	NPC242748
0.573	Remote Similarity	NPC295980
0.5692	Remote Similarity	NPC162742
0.5692	Remote Similarity	NPC304309
0.5692	Remote Similarity	NPC470228
0.5658	Remote Similarity	NPC267510
0.5632	Remote Similarity	NPC86020
0.5595	Remote Similarity	NPC318135
0.5584	Remote Similarity	NPC154452
0.5584	Remote Similarity	NPC121072
0.5543	Remote Similarity	NPC470748
0.5513	Remote Similarity	NPC285231
0.5495	Remote Similarity	NPC94272
0.5476	Remote Similarity	NPC220048
0.5476	Remote Similarity	NPC251614
0.5429	Remote Similarity	NPC153987
0.5376	Remote Similarity	NPC305423
0.5312	Remote Similarity	NPC477809
0.5263	Remote Similarity	NPC98696
0.5263	Remote Similarity	NPC486388
0.5258	Remote Similarity	NPC6806
0.5233	Remote Similarity	NPC165439
0.5217	Remote Similarity	NPC230301
0.5213	Remote Similarity	NPC113044
0.5213	Remote Similarity	NPC283829
0.5213	Remote Similarity	NPC14704
0.5213	Remote Similarity	NPC161676
0.5213	Remote Similarity	NPC600116
0.5181	Remote Similarity	NPC210178
0.5161	Remote Similarity	NPC470432
0.5161	Remote Similarity	NPC230507
0.5161	Remote Similarity	NPC15249
0.5161	Remote Similarity	NPC306991
0.5161	Remote Similarity	NPC25455
0.5147	Remote Similarity	NPC22105
0.5147	Remote Similarity	NPC34019
0.5116	Remote Similarity	NPC489081
0.5102	Remote Similarity	NPC48886
0.5102	Remote Similarity	NPC300557
0.5102	Remote Similarity	NPC94881
0.5072	Remote Similarity	NPC474216
0.5068	Remote Similarity	NPC473943
0.5051	Remote Similarity	NPC480555
0.5051	Remote Similarity	NPC150057
0.5051	Remote Similarity	NPC475182
0.5051	Remote Similarity	NPC147753
0.5051	Remote Similarity	NPC150372
0.505	Remote Similarity	NPC475550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC36744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6885
0.1-0.2	2034
0.2-0.3	197
0.3-0.4	26
0.4-0.5	6
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5217	Remote Similarity	NPD7339	Approved
0.5051	Remote Similarity	NPD8450	Suspended

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