NPASS Compound

Natural Product: NPC124578

Natural Product ID	NPC124578
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DCFZKBTZZMFTED-ZHKQRIMUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10055285
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 91 95 0 0 0 0 0 0 0 0999 V2000 -5.3412 -0.9097 0.9857 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1259 -1.1092 1.4631 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2126 -0.0521 1.8968 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9249 0.8074 2.8998 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9255 -0.5900 2.4909 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8348 -0.6667 1.4068 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4552 0.6056 0.8121 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8526 1.2541 1.1115 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8858 1.9084 2.4702 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0626 2.2687 -0.0247 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1604 2.8396 -0.6168 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4128 2.8320 0.1579 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5755 1.6169 1.0306 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8293 0.8766 0.7558 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4650 0.9912 -0.2399 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6602 2.0774 2.3329 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5078 2.8284 -0.7506 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4638 3.7987 -0.8462 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4025 4.7926 -0.0854 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5994 3.7248 -1.8353 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1190 3.2745 0.2320 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6791 4.5942 0.7654 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7852 3.5729 -1.1294 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2064 2.6413 1.0290 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9414 3.3691 1.7051 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3617 1.1976 0.9813 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0665 0.3888 1.0524 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1544 -0.4375 -0.0833 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4738 -1.7642 0.0964 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6771 -2.1452 1.2757 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5850 -2.7202 -0.9786 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3737 -2.3814 -2.3055 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4915 -3.3421 -3.3024 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8180 -4.6367 -2.9897 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0330 -4.9972 -1.6742 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9088 -4.0234 -0.7094 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1147 0.8930 -0.1763 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3729 0.3685 -0.1261 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9396 0.1239 0.9823 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1413 0.0572 -1.3858 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3530 -1.6250 0.5146 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9879 -2.8947 0.3896 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1016 -3.3589 1.1183 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6323 -3.7442 -0.6106 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6438 -3.2494 -1.4245 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2337 -4.0620 -2.3585 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8412 -5.3955 -2.5194 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8358 -5.8532 -1.6965 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2449 -5.0420 -0.7616 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7077 0.1003 0.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9884 -1.7157 0.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7644 -2.1494 1.5458 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2610 1.0193 3.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8190 0.2988 3.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2199 1.7973 2.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6244 -0.0072 3.3588 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1598 -1.6088 2.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0064 -1.1424 1.9229 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4654 0.5311 -0.3400 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4967 2.9069 2.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9076 1.9237 2.8929 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3284 1.2503 3.1817 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4870 1.6071 -0.8568 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0663 3.9298 -0.8452 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3940 2.4428 -1.6540 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5595 3.7933 0.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1229 2.9458 2.3155 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5690 4.5410 -2.5549 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5227 3.8721 -1.2186 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6380 2.7074 -2.2535 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9419 5.4649 0.0921 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6288 4.7125 0.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2677 4.7859 1.7029 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7339 4.1247 -1.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 2.6280 -1.7036 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0888 4.2505 -1.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0265 0.9151 1.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1802 -0.2199 1.9763 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1201 -1.3738 -2.5511 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3304 -3.0940 -4.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9208 -5.4185 -3.7447 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2924 -6.0027 -1.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0783 -4.3151 0.3189 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3410 0.9897 -1.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1164 -0.3895 -1.1508 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5483 -0.5907 -2.0661 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9322 -2.2202 -1.2861 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0223 -3.6383 -2.9791 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3328 -6.0014 -3.2655 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5030 -6.8850 -1.7920 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4585 -5.4690 -0.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 1 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 13 16 1 1 12 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 10 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 26 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 6 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 14 3 1 0 36 31 1 0 49 44 1 0 13 7 1 0 27 8 1 0 1 50 1 0 1 51 1 0 2 52 1 0 4 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 6 58 1 1 7 59 1 6 9 60 1 0 9 61 1 0 9 62 1 0 10 63 1 6 11 64 1 0 11 65 1 0 12 66 1 1 16 67 1 0 20 68 1 0 20 69 1 0 20 70 1 0 22 71 1 0 22 72 1 0 22 73 1 0 23 74 1 0 23 75 1 0 23 76 1 0 26 77 1 1 27 78 1 1 32 79 1 0 33 80 1 0 34 81 1 0 35 82 1 0 36 83 1 0 40 84 1 0 40 85 1 0 40 86 1 0 45 87 1 0 46 88 1 0 47 89 1 0 48 90 1 0 49 91 1 0 M END

Standard InCHIKey	DCFZKBTZZMFTED-ZHKQRIMUSA-N
Standard InCHI	InChI=1S/C38H42O11/c1-8-36(6)20-25(48-32(42)23-15-11-9-12-16-23)29-37(7)26(19-27(46-21(2)39)38(29,45)34(36)44)35(4,5)30(41)28(47-22(3)40)31(37)49-33(43)24-17-13-10-14-18-24/h8-18,25-29,31,45H,1,19-20H2,2-7H3/t25-,26+,27-,28+,29-,31+,36+,37+,38+/m1/s1
SMILES	C=C[C@@]1(C)C[C@H]([C@@H]2[C@]3(C)[C@@H](C[C@H]([C@]2(C1=O)O)OC(=O)C)C(C)(C)C(=O)[C@@H]([C@@H]3OC(=O)c1ccccc1)OC(=O)C)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	674.27	Volume:	685.44 ? Van der Waals volume.
Dense:	0.984	LogP:	3.595 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.358 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.115 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	35.0
TPSA:	159.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.251	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.114	Fsp³:	0.474
MCE-18:	140.571 ? 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:	0.721	Fluc inhibitor:	0.034 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.101 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.265	Promiscuous compounds:	0.214

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.348	MDCK Permeability:	-4.817
Pgp-inhibitor:	0.998	Pgp-substrate:	0.919
PAMPA:	0.997 ? 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%):	0.996	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	1.0
Plasma Protein Binding (PPB):	92.768%	Volume Distribution (VD):	0.057
Fu:	6.518% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.955	BCRP inhibitor:	0.004
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.013
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.02	CYP3A4-substrate:	0.913
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.997 ? 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):

4.327

Half-life (T1/2):

0.72

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.302
Human Hepatotoxicity (H-HT):	0.144	Drug-induced Liver Injury (DILI):	0.512
AMES Toxicity:	0.216	Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.434	Skin Sensitization:	0.997
Carcinogencity:	0.823	Eye Corrosion:	0.007
Eye Irritation:	0.49	Respiratory Toxicity:	0.253
Drug-induced Neurotoxicity:	0.297	Ototoxicity:	0.149
Hematotoxicity:	0.265	Drug-induced Nephrotoxicity:	0.939
Genotoxicity:	0.989	RPMI-8226 Immunitoxicity:	0.045
A549 Cytotoxicity:	0.243	Hek293 Cytotoxicity:	0.426
BCF:	0.841 ? 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:	3.892 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.636 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.195 ? 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]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654417]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19691312]
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]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31707845]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[385653815]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO1638	Ulmus laciniata	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14797	Orthosiphon aristatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5890	Astragalus inopinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2499	Celmisia petriei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO592	Chroogomphus rutilus	Species	Gomphidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1408	Cirsium helenioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14887	Handroanthus guayacan	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8981	Senecio integerrimus	Species	Asteraceae	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]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8981	Senecio integerrimus	Species	Asteraceae	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]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO14797	Orthosiphon aristatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO592	Chroogomphus rutilus	Species	Gomphidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1638	Ulmus laciniata	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14887	Handroanthus guayacan	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5890	Astragalus inopinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1408	Cirsium helenioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2499	Celmisia petriei	Species	Asteraceae	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 NPC124578 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	7357
0.1-0.2	38916
0.2-0.3	3080
0.3-0.4	471
0.4-0.5	8
0.5-0.6	16
0.6-0.7	8
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
0.7465	Intermediate Similarity	NPC257213
0.7465	Intermediate Similarity	NPC478502
0.6849	Remote Similarity	NPC478503
0.6849	Remote Similarity	NPC237549
0.6757	Remote Similarity	NPC249471
0.6712	Remote Similarity	NPC48568
0.6579	Remote Similarity	NPC473414
0.6447	Remote Similarity	NPC306799
0.6316	Remote Similarity	NPC472030
0.6	Remote Similarity	NPC127857
0.5823	Remote Similarity	NPC228204
0.5769	Remote Similarity	NPC304876
0.5769	Remote Similarity	NPC265395
0.5696	Remote Similarity	NPC60509
0.5625	Remote Similarity	NPC198455
0.557	Remote Similarity	NPC242262
0.557	Remote Similarity	NPC77719
0.55	Remote Similarity	NPC112216
0.55	Remote Similarity	NPC7095
0.5432	Remote Similarity	NPC26033
0.5432	Remote Similarity	NPC469771
0.5375	Remote Similarity	NPC81698
0.5375	Remote Similarity	NPC112523
0.5185	Remote Similarity	NPC165260
0.5181	Remote Similarity	NPC256142
0.5181	Remote Similarity	NPC472022

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC124578 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3196
0.1-0.2	5788
0.2-0.3	166
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