NPASS Compound

Natural Product: NPC478273

Natural Product ID	NPC478273
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LUUJDSKQKMIDDP-YMQJHZQTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	127052738
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 100105 0 0 0 0 0 0 0 0999 V2000 -6.1141 3.4035 -0.0883 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2105 2.3095 0.6329 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2271 2.4196 2.1141 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3019 0.9567 0.0180 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5751 0.2466 0.4817 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1452 -1.1160 0.9830 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8784 -1.3194 0.1801 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0354 -2.4524 0.6477 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6621 -2.3698 0.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0457 -0.9982 0.1301 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7875 -0.7353 1.6015 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9611 0.0741 -0.4162 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3242 1.4145 -0.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 1.4883 -0.7142 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0732 0.3061 -0.2726 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3708 0.4027 -0.6054 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6658 0.8352 -2.0074 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9665 1.4558 0.3113 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4588 1.5878 0.0842 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1634 0.2865 0.3897 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5099 -0.9201 -0.1982 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1290 -1.2960 -1.5289 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9038 -2.0616 0.7630 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3186 -2.0835 0.7119 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0243 -0.8984 -0.2112 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4350 -2.0681 -0.9514 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9980 -2.2079 -0.4140 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7804 -0.9505 -0.7002 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1427 -0.9709 -2.1549 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5038 0.4085 -0.0395 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5779 0.4813 0.8310 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3929 0.4433 2.0712 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9644 0.6050 0.3286 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9806 0.6742 1.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3709 0.7960 0.7908 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8044 0.8549 -0.5151 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1670 0.9737 -0.8133 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1298 1.0369 0.1695 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6975 0.9781 1.4770 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3578 0.8612 1.7751 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4749 1.1546 -0.1499 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2189 0.0297 0.4052 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2724 -1.5538 -1.2425 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0877 -2.7118 -1.2430 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1000 3.3507 -1.1626 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0486 4.3612 0.3895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2537 3.4932 2.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2602 2.0294 2.5190 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0951 1.9417 2.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2936 1.0936 -1.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1323 0.8253 1.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2468 0.1348 -0.4112 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9036 -1.8922 0.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9389 -1.0297 2.0809 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5069 -3.3964 0.2420 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0555 -2.5955 1.7530 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0071 -3.0179 0.7292 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6468 -2.8484 -0.9046 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8795 0.3337 1.8721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6055 -1.2374 2.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8584 -1.2176 1.9689 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2398 -0.1592 -1.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5745 1.9927 0.5549 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8442 2.0303 -1.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4701 2.3775 -0.1442 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7050 1.7604 -1.7785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1199 0.3151 0.8591 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0670 0.3784 -2.7874 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4378 1.9422 -2.0498 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7431 0.7604 -2.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5269 2.4422 0.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.1313 1.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8172 2.3342 0.8241 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7120 2.0017 -0.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2046 0.2302 1.5178 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4071 -1.5401 -2.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7923 -0.4340 -1.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8261 -2.1590 -1.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6009 -3.0476 0.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6254 -1.8338 1.7905 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6729 -2.8692 0.2502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7084 -1.0524 0.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4478 -1.9802 -2.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9409 -2.9805 -0.6645 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9726 -2.4888 0.6349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4802 -3.0345 -0.9763 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3843 -1.5224 -2.7861 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2948 0.0015 -2.6147 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0858 -1.5556 -2.3633 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1591 0.6400 -0.7253 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7475 0.6360 2.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0726 0.8076 -1.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4737 1.0172 -1.8337 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4620 1.0282 2.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0439 0.8166 2.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9359 2.0564 -0.2459 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9773 0.0909 1.4873 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4250 -1.8074 -1.9112 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9150 -0.7562 -1.6688 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5947 -3.5120 -1.4921 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 6 21 23 1 0 23 24 1 0 21 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 20 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 38 41 1 0 12 42 1 0 7 43 1 6 43 44 1 0 42 4 1 0 42 7 1 0 28 10 1 0 40 35 1 0 28 15 1 0 25 16 1 0 1 45 1 0 1 46 1 0 3 47 1 0 3 48 1 0 3 49 1 0 4 50 1 6 5 51 1 0 5 52 1 0 6 53 1 0 6 54 1 0 8 55 1 0 8 56 1 0 9 57 1 0 9 58 1 0 11 59 1 0 11 60 1 0 11 61 1 0 12 62 1 6 13 63 1 0 13 64 1 0 14 65 1 0 14 66 1 0 15 67 1 1 17 68 1 0 17 69 1 0 17 70 1 0 18 71 1 0 18 72 1 0 19 73 1 0 19 74 1 0 20 75 1 1 22 76 1 0 22 77 1 0 22 78 1 0 23 79 1 0 23 80 1 0 24 81 1 0 25 82 1 1 26 83 1 0 26 84 1 0 27 85 1 0 27 86 1 0 29 87 1 0 29 88 1 0 29 89 1 0 33 90 1 0 34 91 1 0 36 92 1 0 37 93 1 0 39 94 1 0 40 95 1 0 41 96 1 0 42 97 1 1 43 98 1 0 43 99 1 0 44100 1 0 M END

Standard InCHIKey	LUUJDSKQKMIDDP-YMQJHZQTSA-N
Standard InCHI	InChI=1S/C39H56O5/c1-25(2)28-15-20-39(24-41)22-21-37(5)29(34(28)39)12-13-31-35(3)18-17-32(36(4,23-40)30(35)16-19-38(31,37)6)44-33(43)14-9-26-7-10-27(42)11-8-26/h7-11,14,28-32,34,40-42H,1,12-13,15-24H2,2-6H3/b14-9+/t28-,29+,30+,31+,32-,34+,35-,36-,37+,38+,39+/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)(CO)[C@@H]5CC[C@@]34C)OC(=O)/C=C/c3ccc(cc3)O)[C@@H]12)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	604.41	Volume:	659.894 ? Van der Waals volume.
Dense:	0.916	LogP:	6.096 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.745 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.821 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	34.0
TPSA:	86.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.174	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.041	Fsp³:	0.718
MCE-18:	155.955 ? 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:	0.947	Fluc inhibitor:	0.981 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.165	Promiscuous compounds:	0.156

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.568	MDCK Permeability:	-5.086
Pgp-inhibitor:	0.283	Pgp-substrate:	0.082
PAMPA:	0.428 ? 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%):	0.794	30% Bioavailability (F30%):	0.968
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.667	MRP1:	0.494
Plasma Protein Binding (PPB):	93.304%	Volume Distribution (VD):	0.16
Fu:	6.355% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.256	BCRP inhibitor:	0.27
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.039	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.069 ? 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):

6.921

Half-life (T1/2):

1.062

ADMET: Toxicity

hERG Blockers:	0.185	hERG Blockers (10um):	0.34
Human Hepatotoxicity (H-HT):	0.711	Drug-induced Liver Injury (DILI):	0.674
AMES Toxicity:	0.494	Rat Oral Acute Toxicity:	0.105
Maximum Recommended Daily Dose:	0.754	Skin Sensitization:	0.997
Carcinogencity:	0.876	Eye Corrosion:	0.004
Eye Irritation:	0.501	Respiratory Toxicity:	0.764
Drug-induced Neurotoxicity:	0.225	Ototoxicity:	0.388
Hematotoxicity:	0.422	Drug-induced Nephrotoxicity:	0.909
Genotoxicity:	0.804	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.262	Hek293 Cytotoxicity:	0.786
BCF:	1.173 ? 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:	4.435 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.946 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.33 ? 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
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19205	Buxus sempervirens	Species	Buxaceae	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

Activity Type	# Activity
IC50	6
Ratio IC50	6

Activity Type	# Activity
Cell line	2
Organism	4
Others	6

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	22000.0	nM	PMID[26722868]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	20000.0	nM	PMID[26722868]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1900.0	nM	PMID[26722868]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2300.0	nM	PMID[26722868]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1600.0	nM	PMID[26722868]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1400.0	nM	PMID[26722868]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	0.7	n.a.	PMID[26722868]
NPT27	Others	Unspecified	n.a.	Ratio IC50	=	9.6	n.a.	PMID[26722868]
NPT27	Others	Unspecified	n.a.	Ratio IC50	>	11.0	n.a.	PMID[26722868]
NPT27	Others	Unspecified	n.a.	Ratio IC50	=	14.0	n.a.	PMID[26722868]
NPT27	Others	Unspecified	n.a.	Ratio IC50	>	14.0	n.a.	PMID[26722868]

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 NPC478273 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	7342
0.1-0.2	37019
0.2-0.3	5029
0.3-0.4	383
0.4-0.5	61
0.5-0.6	13
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8933	High Similarity	NPC310621
0.8272	Intermediate Similarity	NPC478274
0.7975	Intermediate Similarity	NPC148404
0.7975	Intermediate Similarity	NPC35212
0.7059	Intermediate Similarity	NPC252133
0.7024	Intermediate Similarity	NPC478270
0.7024	Intermediate Similarity	NPC478271
0.6786	Remote Similarity	NPC11266
0.6111	Remote Similarity	NPC248287
0.6111	Remote Similarity	NPC234548
0.6053	Remote Similarity	NPC5280
0.5895	Remote Similarity	NPC478272
0.5696	Remote Similarity	NPC168231
0.5682	Remote Similarity	NPC473612
0.5521	Remote Similarity	NPC101863
0.5474	Remote Similarity	NPC8102
0.5474	Remote Similarity	NPC66894
0.5426	Remote Similarity	NPC155192
0.5417	Remote Similarity	NPC486700
0.5417	Remote Similarity	NPC275312
0.5361	Remote Similarity	NPC22676
0.5253	Remote Similarity	NPC482052
0.52	Remote Similarity	NPC205392
0.52	Remote Similarity	NPC105942

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3849
0.1-0.2	5211
0.2-0.3	86
0.3-0.4	3
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