NPASS Compound

Natural Product: NPC482052

Natural Product ID	NPC482052
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WSWPNGAODCKAHB-IFRVZBAOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44584641
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 -6.4532 -2.3291 1.2792 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6481 -0.8641 1.0250 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4588 -0.6969 -0.2389 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5481 -1.0350 -1.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5301 0.0663 -1.4897 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5725 -0.1722 -2.5900 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2230 -0.7133 -2.3808 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6670 -0.5989 -0.9427 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0307 -1.9435 -0.3914 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4478 0.5478 -0.4508 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8289 1.6885 -0.3066 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3855 1.9173 -0.6083 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7271 0.7056 -0.0783 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7533 0.8442 0.1744 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5527 1.2329 -1.0038 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9410 1.9882 1.1914 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3711 2.1391 1.6234 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1200 0.9124 1.9595 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4365 -0.3678 1.6882 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3676 -1.3293 0.9226 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2823 -1.1047 3.0418 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5176 -1.3431 3.6110 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1581 -0.3447 0.9445 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9141 -1.5646 0.0877 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5699 -1.6687 -0.0805 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1750 -0.4754 -0.8541 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6127 -0.6142 -2.2313 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4200 0.8475 1.3790 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6038 0.8682 2.0538 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5601 0.9522 3.3099 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9216 0.7983 1.3949 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0391 0.7103 0.0892 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3316 0.6372 -0.6274 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3509 0.5474 -2.0034 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5530 0.4812 -2.6538 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7750 0.4992 -2.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7119 0.5899 -0.6246 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5201 0.6574 0.0487 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9926 0.4305 -2.6852 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9068 0.5067 -0.1896 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3970 -0.0414 1.0735 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7372 1.0723 2.1157 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4540 -0.7472 1.8488 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4308 1.1835 -2.0419 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5356 2.2106 -1.3462 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0653 1.0149 -3.2403 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6225 -2.9748 0.3951 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0498 -2.7331 2.1292 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3854 -2.5219 1.5953 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3913 -0.5629 1.8382 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3167 -1.3957 -0.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7847 0.3519 -0.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1380 -2.0428 -1.3205 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1270 -1.0122 -2.3556 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5272 0.7652 -3.2465 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1156 -0.8762 -3.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1573 -1.7521 -2.7642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5680 -0.1441 -3.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6307 -2.6686 -1.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0897 -2.1938 -0.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6187 -2.2785 0.5345 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3481 2.6033 0.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0246 2.8851 -0.2832 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2201 1.9130 -1.7312 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1410 0.5472 0.9699 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8370 1.7113 -1.7419 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2480 2.1121 -0.8314 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1852 0.4746 -1.4633 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2968 1.7287 2.0493 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6598 2.9709 0.7616 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9426 2.8302 0.9280 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2994 2.7998 2.5448 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3693 0.9632 3.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1523 -2.3753 1.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3941 -1.1114 -0.1499 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4091 -1.1442 1.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7053 -0.4568 3.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 -2.0297 2.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4588 -2.0917 4.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3662 -0.4322 1.7639 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1724 -2.4397 0.7691 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5422 -1.6831 -0.7706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7983 -2.6290 -0.4928 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9208 -1.4860 0.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1354 -1.4734 -2.7226 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4624 -0.9617 -2.2591 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6416 0.2364 -2.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8012 0.8199 1.9968 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1020 0.6926 -0.4675 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3936 0.5319 -2.5354 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5749 0.4101 -3.7402 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6702 0.6060 -0.0820 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5822 0.7259 1.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6164 -0.3108 -2.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2533 1.6006 -0.1101 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8155 1.6559 2.3108 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0418 0.5526 3.0474 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5009 1.7393 1.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6099 -0.2228 1.9281 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7485 1.6812 -3.5495 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 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 18 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 10 40 1 0 40 41 1 0 41 42 1 0 41 43 1 1 5 44 1 6 44 45 2 0 44 46 1 0 41 2 1 0 40 5 1 0 26 8 1 0 38 33 1 0 26 13 1 0 23 14 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 1 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 9 59 1 0 9 60 1 0 9 61 1 0 11 62 1 0 12 63 1 0 12 64 1 0 13 65 1 1 15 66 1 0 15 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 17 71 1 0 17 72 1 0 18 73 1 1 20 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 21 78 1 0 22 79 1 0 23 80 1 1 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 27 85 1 0 27 86 1 0 27 87 1 0 31 88 1 0 32 89 1 0 34 90 1 0 35 91 1 0 37 92 1 0 38 93 1 0 39 94 1 0 40 95 1 1 42 96 1 0 42 97 1 0 42 98 1 0 43 99 1 0 46100 1 0 M END

Standard InCHIKey	WSWPNGAODCKAHB-IFRVZBAOSA-N
Standard InCHI	InChI=1S/C39H54O7/c1-24-15-20-39(33(43)44)22-21-36(4)27(32(39)38(24,6)45)12-13-29-34(2)18-17-30(35(3,23-40)28(34)16-19-37(29,36)5)46-31(42)14-9-25-7-10-26(41)11-8-25/h7-12,14,24,28-30,32,40-41,45H,13,15-23H2,1-6H3,(H,43,44)/b14-9+/t24-,28-,29-,30+,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)CC[C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)OC(=O)/C=C/c3ccc(cc3)O)[C@@H]2[C@]1(C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.39	Volume:	674.838 ? Van der Waals volume.
Dense:	0.94	LogP:	4.649 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.823 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.642 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	124.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.154	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.142	Fsp³:	0.692
MCE-18:	165.879 ? 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:	0.948	Fluc inhibitor:	0.981 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.222 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.113 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.141	Promiscuous compounds:	0.076

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.711	MDCK Permeability:	-5.201
Pgp-inhibitor:	0.074	Pgp-substrate:	0.001
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):	0.0
20% Bioavailability (F20%):	0.721	30% Bioavailability (F30%):	0.165
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.889
Plasma Protein Binding (PPB):	91.676%	Volume Distribution (VD):	-0.338
Fu:	7.901% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.4	BCRP inhibitor:	0.001
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.06	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.007 ? 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):

2.371

Half-life (T1/2):

1.332

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.056
Human Hepatotoxicity (H-HT):	0.728	Drug-induced Liver Injury (DILI):	0.736
AMES Toxicity:	0.405	Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.697	Skin Sensitization:	0.997
Carcinogencity:	0.892	Eye Corrosion:	0.001
Eye Irritation:	0.227	Respiratory Toxicity:	0.768
Drug-induced Neurotoxicity:	0.176	Ototoxicity:	0.557
Hematotoxicity:	0.265	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	0.975	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.242	Hek293 Cytotoxicity:	0.563
BCF:	0.617 ? 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:	3.921 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.548 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.871 ? 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	=	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 NPC482052 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	7247
0.1-0.2	36635
0.2-0.3	5161
0.3-0.4	612
0.4-0.5	125
0.5-0.6	52
0.6-0.7	15
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8111	Intermediate Similarity	NPC25491
0.7978	Intermediate Similarity	NPC22676
0.7368	Intermediate Similarity	NPC482051
0.7083	Intermediate Similarity	NPC482049
0.7083	Intermediate Similarity	NPC482050
0.7053	Intermediate Similarity	NPC172311
0.7	Intermediate Similarity	NPC481234
0.7	Intermediate Similarity	NPC479431
0.6907	Remote Similarity	NPC178093
0.6667	Remote Similarity	NPC324798
0.6667	Remote Similarity	NPC479742
0.6633	Remote Similarity	NPC304110
0.6633	Remote Similarity	NPC27518
0.6633	Remote Similarity	NPC611516
0.6538	Remote Similarity	NPC481235
0.6531	Remote Similarity	NPC605663
0.6458	Remote Similarity	NPC477874
0.6364	Remote Similarity	NPC479744
0.6275	Remote Similarity	NPC479745
0.6238	Remote Similarity	NPC479739
0.6082	Remote Similarity	NPC155192
0.6044	Remote Similarity	NPC233012
0.6019	Remote Similarity	NPC610795
0.5979	Remote Similarity	NPC485587
0.5941	Remote Similarity	NPC198621
0.5941	Remote Similarity	NPC216940
0.5918	Remote Similarity	NPC173569
0.587	Remote Similarity	NPC54909
0.5843	Remote Similarity	NPC148964
0.5842	Remote Similarity	NPC477873
0.5795	Remote Similarity	NPC136697
0.5769	Remote Similarity	NPC479747
0.5769	Remote Similarity	NPC479746
0.5755	Remote Similarity	NPC479740
0.5755	Remote Similarity	NPC479741
0.5741	Remote Similarity	NPC118033
0.5699	Remote Similarity	NPC327179
0.5686	Remote Similarity	NPC488215
0.5673	Remote Similarity	NPC132126
0.5648	Remote Similarity	NPC601567
0.5648	Remote Similarity	NPC606631
0.5618	Remote Similarity	NPC202728
0.5618	Remote Similarity	NPC158059
0.56	Remote Similarity	NPC248287
0.56	Remote Similarity	NPC234548
0.5588	Remote Similarity	NPC171007
0.5588	Remote Similarity	NPC190849
0.5577	Remote Similarity	NPC488214
0.5556	Remote Similarity	NPC191412
0.5556	Remote Similarity	NPC114159
0.5556	Remote Similarity	NPC6818
0.5472	Remote Similarity	NPC475482
0.5435	Remote Similarity	NPC187933
0.5435	Remote Similarity	NPC157113
0.5429	Remote Similarity	NPC54627
0.5429	Remote Similarity	NPC249817
0.5385	Remote Similarity	NPC247139
0.5333	Remote Similarity	NPC262970
0.5326	Remote Similarity	NPC62516
0.5294	Remote Similarity	NPC182249
0.5294	Remote Similarity	NPC473591
0.5275	Remote Similarity	NPC259733
0.5275	Remote Similarity	NPC158371
0.5275	Remote Similarity	NPC207922
0.5253	Remote Similarity	NPC478273
0.5238	Remote Similarity	NPC101863
0.5221	Remote Similarity	NPC53520
0.5217	Remote Similarity	NPC132824
0.5165	Remote Similarity	NPC235053
0.5158	Remote Similarity	NPC603658
0.5106	Remote Similarity	NPC147232
0.5054	Remote Similarity	NPC35239
0.5051	Remote Similarity	NPC600756
0.5048	Remote Similarity	NPC8102
0.5048	Remote Similarity	NPC66894

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482052 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3571
0.1-0.2	5466
0.2-0.3	106
0.3-0.4	6
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