NPASS Compound

Natural Product: NPC191588

Natural Product ID	NPC191588
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NSLGONDVJPFEEN-LMSCMDSGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 81 85 0 0 0 0 0 0 0 0999 V2000 -4.0893 3.2502 0.7347 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2619 1.9743 1.0206 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5622 1.5165 2.4204 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1558 0.9681 -0.0623 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4587 0.1651 -0.0158 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0486 -1.2951 0.1970 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6767 -1.2553 -0.4822 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8529 -2.4378 -0.1426 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3967 -2.2735 -0.3334 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8370 -0.9450 0.0328 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7629 -0.8876 1.5444 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7515 0.2038 -0.4056 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2242 1.5421 0.0195 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2239 1.7846 -0.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0194 0.5626 0.0547 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5170 0.7228 -0.1023 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9625 0.9296 -1.4881 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8608 2.0020 0.6771 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3342 2.1308 0.9128 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9672 0.9221 1.5081 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6210 -0.3667 0.7862 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0467 -1.5020 1.7001 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1242 -0.4092 0.6603 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5614 -1.7535 0.3233 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4605 -1.7810 -0.6524 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4882 -0.6647 -0.6441 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1497 -0.3680 -2.1151 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3784 -0.5015 -0.4461 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1817 0.3917 -0.7923 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2431 -1.6005 -1.2662 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7564 0.8287 2.8790 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0830 -0.0478 0.1887 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9500 -1.1259 -1.9111 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6545 -0.1530 -2.6281 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6120 -2.1666 -2.6191 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8756 3.5594 -0.2699 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1603 3.9997 1.5055 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9265 0.4923 2.3815 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3415 2.2285 2.8179 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6357 1.6229 3.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9847 1.4681 -1.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9834 0.2828 -0.9943 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1511 0.5259 0.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0246 -1.6053 1.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6966 -1.9099 -0.4527 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1862 -3.3234 -0.7281 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0728 -2.7167 0.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1105 -2.6480 -1.3380 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9117 -3.0186 0.3736 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1674 -1.3702 1.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5771 -1.5552 1.9631 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9648 0.1008 1.9616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8426 0.2435 -1.4988 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7546 2.3031 -0.6352 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5489 1.8312 1.0541 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5438 2.5509 0.5542 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4555 2.2893 -1.1841 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 0.3555 1.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1671 1.5403 -2.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8465 1.6339 -1.5016 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2357 0.0653 -2.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5093 2.8411 0.0703 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3014 1.9830 1.6102 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8822 2.5089 0.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4489 2.9570 1.6758 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0839 1.0395 1.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2928 -2.4113 1.0988 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2767 -1.7896 2.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0082 -1.1887 2.1690 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7770 -0.2141 1.7299 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4202 -2.3707 -0.0535 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2425 -2.3294 1.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9284 -1.9242 -1.6750 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8915 -2.7423 -0.5117 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0489 -2.4963 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0496 -0.6402 -2.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0421 0.6787 -2.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4521 -1.4681 -2.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4186 1.4276 3.3346 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0103 -0.2775 1.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3650 -2.3372 -3.5935 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 21 28 1 0 28 29 2 0 28 30 1 0 20 31 1 0 12 32 1 0 7 33 1 6 33 34 2 0 33 35 1 0 32 4 1 0 32 7 1 0 26 10 1 0 26 15 1 0 23 16 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 6 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 11 51 1 0 11 52 1 0 12 53 1 6 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 1 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 20 66 1 1 22 67 1 0 22 68 1 0 22 69 1 0 23 70 1 1 24 71 1 0 24 72 1 0 25 73 1 0 25 74 1 0 27 75 1 0 27 76 1 0 27 77 1 0 30 78 1 0 31 79 1 0 32 80 1 1 35 81 1 0 M END

Standard InCHIKey	NSLGONDVJPFEEN-LMSCMDSGSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-17(2)18-9-14-30(25(34)35)16-15-27(4)19(23(18)30)7-8-20-26(3)12-11-22(31)29(6,24(32)33)21(26)10-13-28(20,27)5/h18-23,31H,1,7-16H2,2-6H3,(H,32,33)(H,34,35)/t18-,19+,20+,21+,22+,23+,26+,27+,28+,29+,30-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H]([C@@](C)([C@@H]5CC[C@@]34C)C(=O)O)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	3.333 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.855 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.197 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	28.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.416	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.864	Fsp³:	0.867
MCE-18:	107.25 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.939	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.365	Promiscuous compounds:	0.174

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.343	MDCK Permeability:	-5.068
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
PAMPA:	0.994 ? 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%):	0.01	30% Bioavailability (F30%):	0.011
50% Bioavailability (F50%):	0.21

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088	MRP1:	0.996
Plasma Protein Binding (PPB):	96.566%	Volume Distribution (VD):	-0.572
Fu:	4.04% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.938	BCRP inhibitor:	0.01
BSEP inhibitor:	0.296

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.172	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.0 ? 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):

2.324

Half-life (T1/2):

1.734

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.026
Human Hepatotoxicity (H-HT):	0.799	Drug-induced Liver Injury (DILI):	0.841
AMES Toxicity:	0.113	Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.381	Skin Sensitization:	0.971
Carcinogencity:	0.978	Eye Corrosion:	0.297
Eye Irritation:	0.919	Respiratory Toxicity:	0.961
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.587
Hematotoxicity:	0.312	Drug-induced Nephrotoxicity:	0.882
Genotoxicity:	0.461	RPMI-8226 Immunitoxicity:	0.012
A549 Cytotoxicity:	0.017	Hek293 Cytotoxicity:	0.054
BCF:	0.459 ? 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:	3.406 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.894 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.204 ? 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
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1800632]
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]
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]
NPO14532	Salmea scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37278000]
NPO7413	Wedelia biflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9501	Melaleuca leucadendron	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17369	Onobrychis bobrovi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7990	Salsola somalensis	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25947	Bejaranoa semistriata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17753	Carex kobomugi	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17087	Plagiomnium affine	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17753	Carex kobomugi	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7990	Salsola somalensis	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7413	Wedelia biflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25041	Virola bicuhyba	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17087	Plagiomnium affine	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9931	Cryptocarya caloneura	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9501	Melaleuca leucadendron	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15889	Campanula biebersteiniana	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11738	Talaromyces emodensis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14532	Salmea scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29294	Rotheca myricoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1804	Grevillea pyramidalis	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6000	Helichrysum panduratum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17369	Onobrychis bobrovi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25947	Bejaranoa semistriata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12155	Wrightia mollissima	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27844	Coreopsis verticillata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17753	Carex kobomugi	Species	Cyperaceae	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 NPC191588 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	25095
0.1-0.2	21520
0.2-0.3	2740
0.3-0.4	371
0.4-0.5	78
0.5-0.6	29
0.6-0.7	14
0.7-0.8	1
0.8-0.85	0
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	NPC213832
0.7705	Intermediate Similarity	NPC57954
0.7213	Intermediate Similarity	NPC264317
0.7213	Intermediate Similarity	NPC294438
0.7188	Intermediate Similarity	NPC252714
0.7097	Intermediate Similarity	NPC488164
0.7097	Intermediate Similarity	NPC264005
0.7049	Intermediate Similarity	NPC471900
0.6825	Remote Similarity	NPC488506
0.6825	Remote Similarity	NPC220498
0.6364	Remote Similarity	NPC16377
0.6308	Remote Similarity	NPC291373
0.629	Remote Similarity	NPC246445
0.629	Remote Similarity	NPC68828
0.6212	Remote Similarity	NPC201655
0.6176	Remote Similarity	NPC488165
0.6154	Remote Similarity	NPC80590
0.6119	Remote Similarity	NPC151191
0.6061	Remote Similarity	NPC24772
0.6061	Remote Similarity	NPC211162
0.6061	Remote Similarity	NPC183374
0.6	Remote Similarity	NPC192744
0.597	Remote Similarity	NPC271974
0.597	Remote Similarity	NPC277399
0.597	Remote Similarity	NPC195395
0.597	Remote Similarity	NPC247312
0.5882	Remote Similarity	NPC2783
0.5797	Remote Similarity	NPC474719
0.5797	Remote Similarity	NPC269360
0.5797	Remote Similarity	NPC488213
0.5714	Remote Similarity	NPC486704
0.5652	Remote Similarity	NPC4309
0.5634	Remote Similarity	NPC169933
0.5571	Remote Similarity	NPC475061
0.5571	Remote Similarity	NPC601275
0.5522	Remote Similarity	NPC119743
0.5493	Remote Similarity	NPC160506
0.5441	Remote Similarity	NPC30583
0.5417	Remote Similarity	NPC478841
0.5417	Remote Similarity	NPC488166
0.5417	Remote Similarity	NPC607677
0.5316	Remote Similarity	NPC486709
0.5278	Remote Similarity	NPC611139
0.5205	Remote Similarity	NPC600004
0.5205	Remote Similarity	NPC601176
0.5205	Remote Similarity	NPC608379
0.5176	Remote Similarity	NPC475138
0.5143	Remote Similarity	NPC476071
0.5139	Remote Similarity	NPC282616
0.5135	Remote Similarity	NPC132824
0.5122	Remote Similarity	NPC486699

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC191588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6270
0.1-0.2	2817
0.2-0.3	54
0.3-0.4	6
0.4-0.5	1
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7213	Intermediate Similarity	NPD7520	Phase 1
0.5493	Remote Similarity	NPD8035	Phase 2

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