NPASS Compound

Natural Product: NPC73453

Natural Product ID	NPC73453
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CMZFNIMQBCBHEX-KBSLUWATSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	49768308
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 105110 0 0 0 0 0 0 0 0999 V2000 1.7262 -2.7988 2.4035 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6057 -1.8752 1.5286 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9014 -2.6684 1.4359 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8864 -0.6692 2.3543 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0488 0.5290 2.1329 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9122 0.8115 0.6594 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1485 2.1235 0.4419 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1183 1.9888 -0.3129 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9571 0.9162 0.2700 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4132 1.3490 1.6407 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1899 -0.3936 0.3125 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9103 -1.4817 0.5592 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3820 -1.5148 0.7908 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0338 -0.2884 0.3047 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4530 -0.4771 -0.2169 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5895 -1.4253 -1.3361 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1869 -1.0922 0.9885 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6520 -1.1803 0.8214 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3035 -0.2046 -0.0835 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5111 0.9504 -0.5414 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0372 2.2190 0.1517 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8341 1.1774 -2.0235 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2297 1.4241 -2.0368 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0247 0.8811 -0.3938 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2760 1.6411 -1.4330 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8440 1.8407 -0.9981 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1837 0.5576 -0.5767 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7954 -0.1609 -1.8274 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9341 -0.8470 -1.1860 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2047 -1.1483 2.1258 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2436 -0.3627 0.0386 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9841 -1.6394 0.2124 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0075 -1.6789 -0.7755 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2750 1.1106 0.1447 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5842 2.2063 -0.4326 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2902 0.2258 0.2577 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5785 0.4568 -0.2097 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6058 0.5030 0.8821 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8908 -0.2134 0.5278 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2769 -0.1030 -0.9091 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1099 0.1468 -1.8041 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3423 -0.3263 -3.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5133 0.2844 -3.6670 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9557 -0.4008 -1.2420 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3024 0.8289 -1.0541 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8170 -1.5377 0.9702 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8931 1.8268 1.2687 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2662 -3.1323 3.2918 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3138 -3.6161 1.7931 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8861 -2.1677 2.7424 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3925 -2.5109 0.4386 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7642 -3.7445 1.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6470 -2.3313 2.1886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7213 -0.9383 3.4648 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9564 -0.3777 2.3704 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0523 0.2827 2.6008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5251 1.3799 2.6749 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7930 2.8095 -0.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1024 2.6420 1.4116 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6704 2.9436 -0.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1218 1.8573 -1.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5594 0.4994 2.3497 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2604 2.0576 1.6099 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6087 1.9531 2.1618 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3755 -2.4142 0.5852 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8256 -2.4606 0.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5258 -1.6176 1.8878 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2372 0.3523 1.2255 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6943 -1.0028 -2.3378 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4942 -2.0942 -1.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7559 -2.1745 -1.4032 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7879 -2.1098 1.1890 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8842 -0.4552 1.8649 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9261 -2.2135 0.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2124 0.1822 0.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0630 2.0834 0.5148 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8591 3.1159 -0.4399 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3894 2.3152 1.0715 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3839 2.0881 -2.4196 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6913 0.2840 -2.6285 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3637 2.2330 -1.4964 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8005 1.4225 0.5819 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3374 1.2594 -2.4449 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7269 2.6798 -1.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8218 2.6457 -0.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2945 2.2218 -1.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8597 0.2730 -2.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5775 0.0771 -2.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6004 -1.2240 -1.7498 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6708 -1.4154 -0.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9851 -1.7364 2.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2928 -0.1278 -1.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3817 -2.5229 -0.0741 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6169 -1.7104 -1.6874 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5893 1.4865 -0.6773 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2266 0.0057 1.7949 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6953 0.2628 1.1590 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7208 -1.0876 -1.2158 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9592 1.2587 -1.8461 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5482 -1.4146 -3.1595 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4704 -0.1262 -3.8510 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6132 1.1836 -3.2625 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5408 1.2881 -0.2260 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8354 -1.7634 1.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3745 1.8352 2.1235 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 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 19 29 1 0 18 30 1 0 11 31 1 0 31 32 1 0 32 33 1 0 6 34 1 6 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 32 2 1 0 44 37 1 0 31 6 1 0 27 9 1 0 27 14 1 0 24 15 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 10 62 1 0 10 63 1 0 10 64 1 0 12 65 1 0 13 66 1 0 13 67 1 0 14 68 1 1 16 69 1 0 16 70 1 0 16 71 1 0 17 72 1 0 17 73 1 0 18 74 1 6 19 75 1 1 21 76 1 0 21 77 1 0 21 78 1 0 22 79 1 0 22 80 1 0 23 81 1 0 24 82 1 1 25 83 1 0 25 84 1 0 26 85 1 0 26 86 1 0 28 87 1 0 28 88 1 0 28 89 1 0 29 90 1 0 30 91 1 0 31 92 1 6 32 93 1 0 33 94 1 0 37 95 1 6 38 96 1 1 39 97 1 1 40 98 1 6 41 99 1 6 42100 1 0 42101 1 0 43102 1 0 45103 1 0 46104 1 0 47105 1 0 M END

Standard InCHIKey	CMZFNIMQBCBHEX-KBSLUWATSA-N
Standard InCHI	InChI=1S/C36H58O11/c1-31(2)11-13-36(30(45)47-29-26(42)25(41)24(40)20(16-37)46-29)14-12-34(5)18(23(36)28(31)44)7-8-22-32(3)15-19(39)27(43)33(4,17-38)21(32)9-10-35(22,34)6/h7,19-29,37-44H,8-17H2,1-6H3/t19-,20-,21-,22-,23-,24-,25+,26-,27+,28?,29+,32+,33-,34-,35-,36+/m1/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@](C)(CO)[C@@H]5CC[C@@]34C)O)O)[C@@H]2C1O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.4	Volume:	671.293 ? Van der Waals volume.
Dense:	0.993	LogP:	2.095 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.478 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.235 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	197.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.16	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.599	Fsp³:	0.917
MCE-18:	133.507 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.76	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.059 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.133	Promiscuous compounds:	0.017

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.193	MDCK Permeability:	-5.133
Pgp-inhibitor:	0.0	Pgp-substrate:	0.237
PAMPA:	1.0 ? 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):	0.143
20% Bioavailability (F20%):	0.978	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978	MRP1:	0.637
Plasma Protein Binding (PPB):	69.45%	Volume Distribution (VD):	-0.27
Fu:	23.235% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.011
BSEP inhibitor:	0.019

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.023	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.685
HLM stability:	0.044 ? 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):

1.578

Half-life (T1/2):

2.969

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.028
Human Hepatotoxicity (H-HT):	0.614	Drug-induced Liver Injury (DILI):	0.508
AMES Toxicity:	0.79	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.062	Skin Sensitization:	0.996
Carcinogencity:	0.488	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.043
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.992
Hematotoxicity:	0.504	Drug-induced Nephrotoxicity:	0.969
Genotoxicity:	0.656	RPMI-8226 Immunitoxicity:	0.114
A549 Cytotoxicity:	0.406	Hek293 Cytotoxicity:	0.249
BCF:	1.043 ? 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:	3.485 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.05 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.175 ? 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.	stem	n.a.	DOI[10.1016/0031-9422(86)88033-5]
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.	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]
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]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17494	Prunella vulgaris	Species	Lamiaceae	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 NPC73453 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	19969
0.1-0.2	24420
0.2-0.3	4186
0.3-0.4	1013
0.4-0.5	176
0.5-0.6	56
0.6-0.7	18
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC116794
0.8784	High Similarity	NPC605954
0.7975	Intermediate Similarity	NPC68419
0.7875	Intermediate Similarity	NPC271138
0.7875	Intermediate Similarity	NPC102914
0.7875	Intermediate Similarity	NPC110139
0.7875	Intermediate Similarity	NPC108709
0.7778	Intermediate Similarity	NPC220984
0.775	Intermediate Similarity	NPC187056
0.775	Intermediate Similarity	NPC606216
0.775	Intermediate Similarity	NPC607023
0.7662	Intermediate Similarity	NPC191763
0.7059	Intermediate Similarity	NPC256798
0.6905	Remote Similarity	NPC7870
0.6905	Remote Similarity	NPC310014
0.6905	Remote Similarity	NPC269315
0.6905	Remote Similarity	NPC75747
0.686	Remote Similarity	NPC128925
0.6706	Remote Similarity	NPC212968
0.6588	Remote Similarity	NPC199457
0.6471	Remote Similarity	NPC237503
0.6395	Remote Similarity	NPC37739
0.6322	Remote Similarity	NPC137917
0.6322	Remote Similarity	NPC604133
0.6316	Remote Similarity	NPC161674
0.6263	Remote Similarity	NPC134835
0.62	Remote Similarity	NPC73318
0.6163	Remote Similarity	NPC285576
0.6061	Remote Similarity	NPC148417
0.6047	Remote Similarity	NPC167383
0.6022	Remote Similarity	NPC29069
0.5977	Remote Similarity	NPC46388
0.5843	Remote Similarity	NPC65590
0.5843	Remote Similarity	NPC125923
0.5816	Remote Similarity	NPC473343
0.5789	Remote Similarity	NPC179434
0.567	Remote Similarity	NPC139894
0.5667	Remote Similarity	NPC306746
0.5612	Remote Similarity	NPC473373
0.5612	Remote Similarity	NPC150400
0.5604	Remote Similarity	NPC64106
0.5579	Remote Similarity	NPC189884
0.5579	Remote Similarity	NPC90856
0.5579	Remote Similarity	NPC138334
0.551	Remote Similarity	NPC235405
0.5474	Remote Similarity	NPC47063
0.5464	Remote Similarity	NPC48499
0.5455	Remote Similarity	NPC249848
0.5455	Remote Similarity	NPC107966
0.5417	Remote Similarity	NPC204458
0.5417	Remote Similarity	NPC214484
0.5417	Remote Similarity	NPC269095
0.54	Remote Similarity	NPC295371
0.5392	Remote Similarity	NPC109588
0.5392	Remote Similarity	NPC30735
0.5385	Remote Similarity	NPC190837
0.5368	Remote Similarity	NPC209894
0.5361	Remote Similarity	NPC78046
0.5333	Remote Similarity	NPC601659
0.5327	Remote Similarity	NPC96641
0.5327	Remote Similarity	NPC163183
0.5288	Remote Similarity	NPC235438
0.5248	Remote Similarity	NPC473884
0.5248	Remote Similarity	NPC39211
0.5222	Remote Similarity	NPC240125
0.52	Remote Similarity	NPC475516
0.5196	Remote Similarity	NPC475171
0.5196	Remote Similarity	NPC469946
0.5192	Remote Similarity	NPC10607
0.5192	Remote Similarity	NPC102439
0.5192	Remote Similarity	NPC101744
0.5192	Remote Similarity	NPC46665
0.5185	Remote Similarity	NPC481030
0.5149	Remote Similarity	NPC58448
0.5143	Remote Similarity	NPC475591
0.5143	Remote Similarity	NPC236870
0.5143	Remote Similarity	NPC68175
0.514	Remote Similarity	NPC281148
0.5106	Remote Similarity	NPC48249
0.5098	Remote Similarity	NPC157868
0.5096	Remote Similarity	NPC309714
0.5094	Remote Similarity	NPC222580
0.5048	Remote Similarity	NPC40775
0.5048	Remote Similarity	NPC11551
0.5048	Remote Similarity	NPC480475
0.5046	Remote Similarity	NPC80986
0.5042	Remote Similarity	NPC136768

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC73453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7177
0.1-0.2	1905
0.2-0.3	65
0.3-0.4	3
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