NPASS Compound

Natural Product: NPC83157

Natural Product ID	NPC83157
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BDHQMRXFDYJGII-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	544165
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 84 88 0 0 0 0 0 0 0 0999 V2000 7.9772 0.2376 -1.3715 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7113 0.4074 -0.5764 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8917 1.6543 0.2775 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5365 -0.7437 0.3384 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3637 -1.7832 0.3461 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3900 -0.7820 1.3097 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1427 -0.7170 0.4801 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8852 -0.7534 1.3873 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0128 -2.0748 2.1105 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7007 -0.6304 0.5089 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5340 -1.7372 -0.5079 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0966 -1.4369 -0.9525 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5898 -1.2718 0.3583 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8162 -2.6596 0.9231 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9859 -0.6945 0.2313 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7920 -1.5632 -0.6770 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9320 -0.8508 -1.3608 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4001 0.3731 -0.6402 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5703 0.9455 -1.3806 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6468 -0.1355 -1.4956 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2489 1.4106 -2.7630 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1060 2.1326 -0.6090 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9897 3.1504 -0.5372 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7681 2.5756 0.1642 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2632 1.3301 -0.5225 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0927 1.3400 -1.4014 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9884 0.7419 -0.0815 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3402 1.4414 1.1048 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0892 1.0524 1.0883 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3607 -0.4386 1.1637 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3296 -0.7719 2.6305 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1890 2.7263 -1.2185 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1119 1.1453 -2.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9559 -0.6224 -2.0520 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8539 0.1446 -0.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8725 0.5266 -1.2841 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7564 1.4763 0.9547 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9784 1.8387 0.8414 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1617 2.4949 -0.4145 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2495 -2.6257 1.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1907 -1.7571 -0.3668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4436 0.1818 1.8977 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4461 -1.6408 1.9746 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1143 -1.5304 -0.2470 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1077 0.2419 -0.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0322 0.0640 2.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0692 -2.6009 2.2799 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4403 -1.8648 3.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7749 -2.7458 1.6326 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9260 0.2771 -0.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2124 -1.6095 -1.3770 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5389 -2.7430 -0.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2015 -2.3378 -1.5230 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0437 -0.5139 -1.5303 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0657 -3.2110 1.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3733 -3.2150 0.1100 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5423 -2.6553 1.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4375 -0.8134 1.2633 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2384 -2.4241 -0.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2096 -2.0524 -1.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6468 -0.5882 -2.4222 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7923 -1.5467 -1.4654 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7645 0.0637 0.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6523 0.3085 -1.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4505 -0.6641 -2.4536 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5130 -0.8530 -0.6422 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3123 0.5692 -3.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0277 2.1713 -3.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2536 1.8441 -2.8814 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3546 1.8255 0.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6476 3.4743 -1.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2966 4.0540 0.0127 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0119 3.4058 0.1502 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0371 2.2771 1.2020 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0349 0.6874 -2.2986 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5591 2.3076 -1.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8158 1.1311 2.0571 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4026 2.5292 1.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6288 1.5298 1.9268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5151 1.4289 0.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0556 -1.7835 2.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4145 -0.0682 3.1071 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2871 -0.5124 3.0858 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0339 2.5061 -0.7387 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 2 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 22 32 1 0 30 10 1 0 30 13 1 0 27 15 1 0 25 18 1 0 27 25 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 9 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 14 55 1 0 14 56 1 0 14 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 0 20 64 1 0 20 65 1 0 20 66 1 0 21 67 1 0 21 68 1 0 21 69 1 0 22 70 1 0 23 71 1 0 23 72 1 0 24 73 1 0 24 74 1 0 26 75 1 0 26 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 29 80 1 0 31 81 1 0 31 82 1 0 31 83 1 0 32 84 1 0 M END

Standard InCHIKey	BDHQMRXFDYJGII-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C31H52O/c1-20(2)21(3)9-10-22(4)23-13-15-29(8)25-12-11-24-27(5,6)26(32)14-16-30(24)19-31(25,30)18-17-28(23,29)7/h20,22-26,32H,3,9-19H2,1-2,4-8H3
SMILES	CC(C)C(=C)CCC(C)C1CCC2(C)C3CCC4C(C)(C)C(CCC54CC35CCC12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.4	Volume:	508.103 ? Van der Waals volume.
Dense:	0.867	LogP:	7.707 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.237 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.217 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.425	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.447	Fsp³:	0.935
MCE-18:	133.2 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.534	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.008 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.624	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.893	MDCK Permeability:	-4.783
Pgp-inhibitor:	0.487	Pgp-substrate:	0.0
PAMPA:	0.0 ? 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%):	0.038	30% Bioavailability (F30%):	0.475
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.53	MRP1:	1.0
Plasma Protein Binding (PPB):	91.696%	Volume Distribution (VD):	0.198
Fu:	6.502% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.156
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.259
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.595	CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.919	CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.746	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	1.0
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):

15.529

Half-life (T1/2):

0.617

ADMET: Toxicity

hERG Blockers:	0.324	hERG Blockers (10um):	0.742
Human Hepatotoxicity (H-HT):	0.518	Drug-induced Liver Injury (DILI):	0.015
AMES Toxicity:	0.109	Rat Oral Acute Toxicity:	0.2
Maximum Recommended Daily Dose:	0.626	Skin Sensitization:	0.247
Carcinogencity:	0.275	Eye Corrosion:	0.067
Eye Irritation:	0.739	Respiratory Toxicity:	0.767
Drug-induced Neurotoxicity:	0.257	Ototoxicity:	0.812
Hematotoxicity:	0.134	Drug-induced Nephrotoxicity:	0.071
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.141	Hek293 Cytotoxicity:	0.246
BCF:	2.1 ? 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:	5.439 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.654 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.293 ? 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
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	branch	n.a.	PMID[17202693]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36362399]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38358042]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	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 NPC83157 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	27856
0.1-0.2	19006
0.2-0.3	2460
0.3-0.4	381
0.4-0.5	97
0.5-0.6	23
0.6-0.7	16
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC254509
0.8261	Intermediate Similarity	NPC607543
0.8125	Intermediate Similarity	NPC472342
0.7959	Intermediate Similarity	NPC70982
0.7708	Intermediate Similarity	NPC331618
0.7708	Intermediate Similarity	NPC257191
0.7708	Intermediate Similarity	NPC196358
0.76	Intermediate Similarity	NPC49168
0.76	Intermediate Similarity	NPC5046
0.7551	Intermediate Similarity	NPC200243
0.7308	Intermediate Similarity	NPC195489
0.7292	Intermediate Similarity	NPC41577
0.72	Intermediate Similarity	NPC85346
0.72	Intermediate Similarity	NPC65897
0.72	Intermediate Similarity	NPC80237
0.72	Intermediate Similarity	NPC604180
0.7143	Intermediate Similarity	NPC299948
0.7143	Intermediate Similarity	NPC241085
0.7115	Intermediate Similarity	NPC76518
0.7091	Intermediate Similarity	NPC483817
0.6731	Remote Similarity	NPC470830
0.6731	Remote Similarity	NPC195530
0.6731	Remote Similarity	NPC479659
0.6731	Remote Similarity	NPC273366
0.6545	Remote Similarity	NPC89747
0.6538	Remote Similarity	NPC82623
0.6481	Remote Similarity	NPC472341
0.6333	Remote Similarity	NPC146937
0.6296	Remote Similarity	NPC473279
0.6296	Remote Similarity	NPC22133
0.625	Remote Similarity	NPC473238
0.6111	Remote Similarity	NPC107704
0.6071	Remote Similarity	NPC230704
0.6034	Remote Similarity	NPC18384
0.6034	Remote Similarity	NPC110923
0.6034	Remote Similarity	NPC74296
0.5965	Remote Similarity	NPC134481
0.5893	Remote Similarity	NPC189917
0.5893	Remote Similarity	NPC96812
0.5893	Remote Similarity	NPC67872
0.5893	Remote Similarity	NPC39462
0.5833	Remote Similarity	NPC195366
0.5833	Remote Similarity	NPC114743
0.5818	Remote Similarity	NPC145552
0.5789	Remote Similarity	NPC12722
0.5667	Remote Similarity	NPC47808
0.5574	Remote Similarity	NPC85379
0.5574	Remote Similarity	NPC144909
0.5574	Remote Similarity	NPC476304
0.55	Remote Similarity	NPC476186
0.5469	Remote Similarity	NPC288906
0.5439	Remote Similarity	NPC302041
0.5424	Remote Similarity	NPC606508
0.541	Remote Similarity	NPC307776
0.5345	Remote Similarity	NPC118508
0.5263	Remote Similarity	NPC69149
0.5254	Remote Similarity	NPC477858
0.5085	Remote Similarity	NPC113978
0.5075	Remote Similarity	NPC266431

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC83157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8101
0.1-0.2	984
0.2-0.3	64
0.3-0.4	1
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