NPASS Compound

Natural Product: NPC482049

Natural Product ID	NPC482049
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SWEBUECVVVXRRV-NUKDMGCPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44584638
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 101106 0 0 0 0 0 0 0 0999 V2000 -8.0417 0.7803 1.5220 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4858 0.7332 0.1305 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7889 -0.6677 -0.4169 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0221 -1.5882 0.4931 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5562 -1.4208 0.1708 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8227 -1.5812 1.4776 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3615 -1.7340 1.1799 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8108 -0.5001 0.5509 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6201 0.5032 1.6779 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7524 0.1483 -0.4157 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2508 1.0243 -1.2805 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8319 1.4238 -1.3735 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9261 0.5923 -0.5085 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5025 0.5977 -0.9817 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7446 0.1912 -2.3697 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9712 2.0572 -0.8295 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4063 2.2299 -1.1466 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2954 1.0818 -0.8674 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7584 0.0353 0.0437 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4634 -1.2819 -0.3201 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2802 0.3149 1.4688 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6886 0.2687 1.4230 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5011 0.4715 2.5150 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9881 0.7123 3.6254 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9505 0.4060 2.3776 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5248 0.1543 1.2205 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9526 0.0722 0.9994 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4263 -0.1982 -0.2650 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7948 -0.2868 -0.5269 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7075 -0.1012 0.4957 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2487 0.1670 1.7507 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8722 0.2513 1.9910 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0576 -0.2010 0.1765 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2959 -0.1392 0.0708 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8302 -1.5916 0.1837 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5758 -1.5420 0.6980 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5065 -0.7420 -0.1889 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7490 -1.6015 -1.3982 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8151 0.4778 -2.0388 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8368 3.4207 -0.5138 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2042 -0.1168 -0.4536 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0020 1.0329 0.0825 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8739 2.3147 -0.6702 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6268 1.3143 1.4092 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2211 -2.5812 -0.7123 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8456 -2.3706 -1.8820 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3134 -3.8765 -0.2764 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2702 0.6054 2.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5591 1.7647 1.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8315 0.0137 1.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0992 1.4168 -0.4892 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4567 -0.7734 -1.4527 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8763 -0.8166 -0.2773 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2185 -1.2861 1.5407 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3688 -2.6397 0.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1400 -2.5342 1.9935 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0618 -0.7893 2.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1820 -2.6790 0.6871 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8699 -1.8453 2.1985 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3567 0.2721 2.5052 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6422 0.4233 2.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8689 1.5339 1.3612 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9146 1.4934 -2.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4279 1.4121 -2.4031 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7764 2.5194 -1.0864 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8818 1.1619 0.4714 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3795 -0.7112 -2.4973 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1445 -0.0043 -3.0059 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 0.9904 -2.9637 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8136 2.2875 0.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3420 2.7434 -1.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4956 2.4671 -2.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2263 1.5143 -0.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9510 -1.8423 -1.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5127 -1.1219 -0.5873 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4666 -1.9283 0.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8478 -0.4898 2.0979 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9429 1.2901 1.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6104 0.5649 3.2367 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8145 0.0012 0.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7682 -0.3533 -1.1065 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1423 -0.4993 -1.5242 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9331 0.3150 2.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5815 0.4656 3.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7444 -0.2215 0.8990 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9155 0.3152 1.0397 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9484 -2.1378 -0.7568 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4565 -2.0573 0.9638 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0064 -2.5872 0.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5324 -1.1998 1.7378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3769 -1.1609 -2.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7961 -1.9647 -1.8456 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2451 -2.5341 -1.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4604 1.0754 -2.4894 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6574 3.3796 0.4598 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4738 -0.1986 -1.5492 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1330 2.2607 -1.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7058 2.9755 -0.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9677 2.9099 -0.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0977 2.1486 1.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7394 -4.5999 -0.7373 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 19 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 6 18 39 1 0 17 40 1 0 10 41 1 0 41 42 1 0 42 43 1 0 42 44 1 1 5 45 1 6 45 46 2 0 45 47 1 0 42 2 1 0 41 5 1 0 37 8 1 0 37 13 1 0 34 14 1 0 32 27 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 6 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 9 60 1 0 9 61 1 0 9 62 1 0 11 63 1 0 12 64 1 0 12 65 1 0 13 66 1 1 15 67 1 0 15 68 1 0 15 69 1 0 16 70 1 0 16 71 1 0 17 72 1 6 18 73 1 1 20 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 21 78 1 0 25 79 1 0 26 80 1 0 28 81 1 0 29 82 1 0 31 83 1 0 32 84 1 0 33 85 1 0 34 86 1 1 35 87 1 0 35 88 1 0 36 89 1 0 36 90 1 0 38 91 1 0 38 92 1 0 38 93 1 0 39 94 1 0 40 95 1 0 41 96 1 6 43 97 1 0 43 98 1 0 43 99 1 0 44100 1 0 47101 1 0 M END

Standard InCHIKey	SWEBUECVVVXRRV-NUKDMGCPSA-N
Standard InCHI	InChI=1S/C39H54O8/c1-23-15-18-39(33(44)45)20-19-36(4)26(31(39)38(23,6)46)12-13-29-34(2)21-27(41)32(43)35(3,28(34)16-17-37(29,36)5)22-47-30(42)14-9-24-7-10-25(40)11-8-24/h7-12,14,23,27-29,31-32,40-41,43,46H,13,15-22H2,1-6H3,(H,44,45)/b14-9+/t23-,27-,28-,29-,31-,32+,34+,35+,36-,37-,38-,39+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(COC(=O)/C=C/c6ccc(cc6)O)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@]1(C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.38	Volume:	683.628 ? Van der Waals volume.
Dense:	0.951	LogP:	3.318 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.016 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.467 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	144.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.294	Fsp³:	0.692
MCE-18:	169.485 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.903	Fluc inhibitor:	0.97 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.271 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.076 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.113	Promiscuous compounds:	0.078

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.711	MDCK Permeability:	-5.155
Pgp-inhibitor:	0.001	Pgp-substrate:	0.011
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):	0.001
20% Bioavailability (F20%):	0.72	30% Bioavailability (F30%):	0.405
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.868
Plasma Protein Binding (PPB):	89.466%	Volume Distribution (VD):	-0.386
Fu:	9.322% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.964	BCRP inhibitor:	0.0
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.253
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.003 ? 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):

1.899

Half-life (T1/2):

1.79

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.05
Human Hepatotoxicity (H-HT):	0.677	Drug-induced Liver Injury (DILI):	0.686
AMES Toxicity:	0.388	Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.639	Skin Sensitization:	0.973
Carcinogencity:	0.782	Eye Corrosion:	0.0
Eye Irritation:	0.146	Respiratory Toxicity:	0.577
Drug-induced Neurotoxicity:	0.05	Ototoxicity:	0.793
Hematotoxicity:	0.227	Drug-induced Nephrotoxicity:	0.974
Genotoxicity:	0.962	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.153	Hek293 Cytotoxicity:	0.385
BCF:	0.549 ? 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:	3.689 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.35 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.674 ? 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
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1279126]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]

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
Activity	6
TC50	1

Activity Type	# Activity
Cell line	1
Organism	4
Others	2

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
NPT1452	Cell line	C8166	Homo sapiens	TC50	=	30.0	ug ml-1	PMID[1279126]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	0.0	%	PMID[1279126]
NPT2517	Organism	Human rhinovirus 1B	Human rhinovirus 1B	Activity	=	100.0	%	PMID[1279126]
NPT27	Others	Unspecified	n.a.	Activity	=	50.0	ug ml-1	PMID[1279126]
NPT27	Others	Unspecified	n.a.	Activity	=	20.0	ug ml-1	PMID[1279126]
NPT338	Organism	Sindbis virus	Sindbis virus	Activity	=	100.0	%	PMID[1279126]

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 NPC482049 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	7605
0.1-0.2	36970
0.2-0.3	4715
0.3-0.4	398
0.4-0.5	95
0.5-0.6	48
0.6-0.7	17
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	NPC482050
0.8242	Intermediate Similarity	NPC479747
0.8242	Intermediate Similarity	NPC479746
0.7789	Intermediate Similarity	NPC479740
0.7789	Intermediate Similarity	NPC479741
0.7368	Intermediate Similarity	NPC25491
0.7083	Intermediate Similarity	NPC482052
0.6979	Remote Similarity	NPC198621
0.6979	Remote Similarity	NPC216940
0.67	Remote Similarity	NPC482051
0.6444	Remote Similarity	NPC96693
0.6381	Remote Similarity	NPC481234
0.6381	Remote Similarity	NPC479431
0.6207	Remote Similarity	NPC259733
0.6207	Remote Similarity	NPC158371
0.6207	Remote Similarity	NPC207922
0.6186	Remote Similarity	NPC139243
0.6186	Remote Similarity	NPC116742
0.6136	Remote Similarity	NPC247139
0.6078	Remote Similarity	NPC54627
0.6078	Remote Similarity	NPC249817
0.6019	Remote Similarity	NPC304110
0.6019	Remote Similarity	NPC27518
0.6019	Remote Similarity	NPC611516
0.598	Remote Similarity	NPC262970
0.5963	Remote Similarity	NPC481235
0.5962	Remote Similarity	NPC475482
0.5962	Remote Similarity	NPC178093
0.5922	Remote Similarity	NPC605663
0.5769	Remote Similarity	NPC172311
0.5769	Remote Similarity	NPC479744
0.5755	Remote Similarity	NPC324798
0.5755	Remote Similarity	NPC479742
0.5667	Remote Similarity	NPC202728
0.5667	Remote Similarity	NPC158059
0.5619	Remote Similarity	NPC488214
0.5588	Remote Similarity	NPC235557
0.5579	Remote Similarity	NPC233012
0.5577	Remote Similarity	NPC22676
0.5543	Remote Similarity	NPC62516
0.5514	Remote Similarity	NPC479739
0.5495	Remote Similarity	NPC136697
0.5484	Remote Similarity	NPC187933
0.5484	Remote Similarity	NPC157113
0.5435	Remote Similarity	NPC35239
0.5435	Remote Similarity	NPC191412
0.5435	Remote Similarity	NPC114159
0.5435	Remote Similarity	NPC132824
0.5435	Remote Similarity	NPC6818
0.5421	Remote Similarity	NPC145527
0.5421	Remote Similarity	NPC208785
0.5417	Remote Similarity	NPC54909
0.5413	Remote Similarity	NPC479745
0.5376	Remote Similarity	NPC148964
0.5368	Remote Similarity	NPC603658
0.5333	Remote Similarity	NPC271494
0.5268	Remote Similarity	NPC310729
0.5268	Remote Similarity	NPC150310
0.5221	Remote Similarity	NPC118033
0.5179	Remote Similarity	NPC206232
0.5179	Remote Similarity	NPC14515
0.5161	Remote Similarity	NPC256247
0.5158	Remote Similarity	NPC284865
0.5138	Remote Similarity	NPC132126
0.5133	Remote Similarity	NPC601567
0.5133	Remote Similarity	NPC606631
0.5094	Remote Similarity	NPC477874
0.5053	Remote Similarity	NPC118964
0.5047	Remote Similarity	NPC171007
0.5047	Remote Similarity	NPC190849
0.5045	Remote Similarity	NPC473773
0.5045	Remote Similarity	NPC475579

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3385
0.1-0.2	5664
0.2-0.3	99
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