NPASS Compound

Natural Product: NPC212607

Natural Product ID	NPC212607
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OTDUGESKRJHFHR-CEFFGXRLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10028395
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 85 89 0 0 0 0 0 0 0 0999 V2000 -5.3754 0.5869 2.9795 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9795 0.5057 1.4938 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7933 1.6287 0.8338 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4764 -0.7996 1.0007 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7614 -1.3894 -0.1442 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4828 -0.7325 -0.5474 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6785 -1.8108 -1.2899 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3498 -1.2543 -1.6813 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5557 -0.9536 -0.4031 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3529 -2.2785 0.2839 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3306 0.0208 0.4344 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8246 1.1224 0.9569 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6137 1.5405 0.7727 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3729 0.2536 0.4763 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8314 0.3750 0.5237 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1268 1.7128 1.2299 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4043 -0.6913 1.4306 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7942 -0.3115 1.7755 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6718 -0.1192 0.5838 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0398 0.2157 -0.7016 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7933 1.4623 -1.2359 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5373 -0.8491 -1.7136 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5616 0.3810 -0.7915 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9093 -0.4458 -1.8669 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7059 -1.2364 -1.4012 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7557 -0.2893 -0.7706 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4026 0.7765 -1.7800 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6416 0.8371 1.0009 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2816 -1.3411 2.6250 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7613 -0.2942 0.6798 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5268 0.7536 1.3901 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7642 0.3275 -1.5253 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4960 1.5322 -1.4392 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4194 -0.0719 -2.7067 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7424 0.8575 -3.7194 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4448 0.3340 3.0750 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8037 -0.2270 3.4771 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1155 1.5855 3.3693 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1495 1.2966 -0.1722 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6791 1.8903 1.4111 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1812 2.5464 0.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5539 -1.5381 1.8534 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5574 -0.6589 0.6984 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3999 -1.4498 -1.0635 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5273 -2.4701 0.0874 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5980 -2.7102 -0.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2350 -2.0884 -2.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4879 -0.3816 -2.3144 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7963 -2.0166 -2.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6586 -2.4020 0.7136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1078 -2.3587 1.0907 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5107 -3.1469 -0.3903 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4852 1.7698 1.5559 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9050 1.9839 1.7447 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6670 2.2779 -0.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0272 -0.4319 1.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1689 2.0110 1.1594 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5571 2.5259 0.6884 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8580 1.6643 2.3011 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7946 -0.6356 2.3802 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3917 -1.6958 1.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7933 0.5871 2.4632 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3044 -1.0617 0.5304 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1933 1.8057 -2.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8163 1.1885 -1.5675 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9067 2.2276 -0.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2398 -1.8503 -1.4361 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4251 -0.5237 -2.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6602 -0.8290 -1.5346 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4121 1.4559 -1.1412 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5584 -1.1931 -2.3462 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5289 0.1745 -2.7351 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9512 -2.1335 -0.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2160 -1.6087 -2.3507 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5667 1.2564 -1.5337 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1378 1.5752 -1.8753 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3815 0.2660 -2.7868 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2664 0.4366 1.6393 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2343 -2.2126 2.1186 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7471 -1.1973 1.3659 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3798 1.7317 0.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0927 0.9790 2.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8028 1.3851 -3.9807 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5129 1.5414 -3.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0911 0.3041 -4.6011 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 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 19 28 1 0 18 29 1 0 11 30 1 0 30 31 1 0 6 32 1 6 32 33 2 0 32 34 1 0 34 35 1 0 31 2 1 0 30 6 1 0 26 9 1 0 26 14 1 0 23 15 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 10 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 16 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 1 19 63 1 6 21 64 1 0 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 22 69 1 0 23 70 1 0 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 28 78 1 0 29 79 1 0 30 80 1 0 31 81 1 0 31 82 1 0 35 83 1 0 35 84 1 0 35 85 1 0 M END

Standard InCHIKey	OTDUGESKRJHFHR-CEFFGXRLSA-N
Standard InCHI	InChI=1S/C31H50O4/c1-26(2)13-15-31(25(34)35-8)16-14-29(6)19(20(31)17-26)9-10-23-28(5)18-21(32)24(33)27(3,4)22(28)11-12-30(23,29)7/h9,20-24,32-33H,10-18H2,1-8H3/t20?,21-,22?,23?,24+,28+,29-,30-,31+/m1/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CCC4[C@@]5(C)C[C@H]([C@@H](C(C)(C)C5CC[C@@]34C)O)O)C2C1)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.37	Volume:	531.838 ? Van der Waals volume.
Dense:	0.915	LogP:	4.18 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.03 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.3 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.337	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.801	Fsp³:	0.903
MCE-18:	107.119 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.774	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.011 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.312	Promiscuous compounds:	0.022

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.045	MDCK Permeability:	-4.913
Pgp-inhibitor:	0.031	Pgp-substrate:	0.007
PAMPA:	0.941 ? 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%):	0.145	30% Bioavailability (F30%):	0.053
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985	MRP1:	0.941
Plasma Protein Binding (PPB):	94.148%	Volume Distribution (VD):	0.202
Fu:	6.851% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.218
BSEP inhibitor:	0.984

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.624
CYP2C19-inhibitor:	0.904	CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.519
CYP3A4-inhibitor:	0.791	CYP3A4-substrate:	0.04
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.885
HLM stability:	0.846 ? 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):

7.601

Half-life (T1/2):

0.62

ADMET: Toxicity

hERG Blockers:	0.122	hERG Blockers (10um):	0.31
Human Hepatotoxicity (H-HT):	0.626	Drug-induced Liver Injury (DILI):	0.112
AMES Toxicity:	0.057	Rat Oral Acute Toxicity:	0.25
Maximum Recommended Daily Dose:	0.662	Skin Sensitization:	0.374
Carcinogencity:	0.492	Eye Corrosion:	0.0
Eye Irritation:	0.041	Respiratory Toxicity:	0.467
Drug-induced Neurotoxicity:	0.018	Ototoxicity:	0.787
Hematotoxicity:	0.069	Drug-induced Nephrotoxicity:	0.393
Genotoxicity:	0.173	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.156	Hek293 Cytotoxicity:	0.271
BCF:	2.745 ? 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:	4.978 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.137 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.893 ? 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
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	DOI[10.1016/j.tetlet.2016.12.029]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/np50070a005]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	leaves	Botanical Garden of Innsbruck, Austria	n.a.	PMID[20100662]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21923134]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38732062]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	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 NPC212607 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	18942
0.1-0.2	26253
0.2-0.3	3779
0.3-0.4	628
0.4-0.5	198
0.5-0.6	42
0.6-0.7	5
0.7-0.8	0
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	NPC136313
0.7705	Intermediate Similarity	NPC246708
0.7344	Intermediate Similarity	NPC259788
0.7344	Intermediate Similarity	NPC255589
0.7344	Intermediate Similarity	NPC481361
0.7077	Intermediate Similarity	NPC307335
0.7077	Intermediate Similarity	NPC74855
0.6462	Remote Similarity	NPC267517
0.6406	Remote Similarity	NPC478657
0.6269	Remote Similarity	NPC162107
0.6269	Remote Similarity	NPC46912
0.6087	Remote Similarity	NPC488519
0.5909	Remote Similarity	NPC235341
0.5821	Remote Similarity	NPC470588
0.5781	Remote Similarity	NPC290598
0.5781	Remote Similarity	NPC30590
0.5769	Remote Similarity	NPC167383
0.5714	Remote Similarity	NPC214756
0.5634	Remote Similarity	NPC84319
0.5634	Remote Similarity	NPC306541
0.5634	Remote Similarity	NPC52021
0.5634	Remote Similarity	NPC599947
0.5556	Remote Similarity	NPC258130
0.5541	Remote Similarity	NPC481363
0.5522	Remote Similarity	NPC101475
0.5522	Remote Similarity	NPC34177
0.55	Remote Similarity	NPC605954
0.5488	Remote Similarity	NPC310014
0.5488	Remote Similarity	NPC68419
0.5488	Remote Similarity	NPC269315
0.5429	Remote Similarity	NPC40552
0.5366	Remote Similarity	NPC199457
0.5301	Remote Similarity	NPC7870
0.5301	Remote Similarity	NPC75747
0.5301	Remote Similarity	NPC604133
0.5278	Remote Similarity	NPC96916
0.5263	Remote Similarity	NPC488520
0.5244	Remote Similarity	NPC237503
0.5217	Remote Similarity	NPC253807
0.5217	Remote Similarity	NPC195334
0.5217	Remote Similarity	NPC158662
0.5135	Remote Similarity	NPC472149
0.5135	Remote Similarity	NPC71074
0.5135	Remote Similarity	NPC37221
0.5135	Remote Similarity	NPC605937
0.5128	Remote Similarity	NPC488522
0.5114	Remote Similarity	NPC214484
0.5075	Remote Similarity	NPC601696
0.5072	Remote Similarity	NPC196753
0.5068	Remote Similarity	NPC191965
0.5068	Remote Similarity	NPC172361
0.5067	Remote Similarity	NPC259733
0.5067	Remote Similarity	NPC158371
0.5067	Remote Similarity	NPC207922

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC212607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6968
0.1-0.2	2103
0.2-0.3	76
0.3-0.4	2
0.4-0.5	1
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