NPASS Compound

Natural Product: NPC488524

Natural Product ID	NPC488524
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AOKGWENYNIEUGE-GHMKDZOHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10674596
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 99103 0 0 0 0 0 0 0 0999 V2000 10.6657 -0.8023 -0.7219 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6996 -1.8401 -0.2425 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3861 -1.8287 -0.9528 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7164 -0.4728 -0.7562 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4040 -0.4289 -1.4493 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3248 -0.4985 -2.6796 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2802 -0.3100 -0.6947 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9393 -0.2544 -1.2145 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2532 -1.4642 -0.7360 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7802 -1.3783 -0.4810 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3796 -0.1121 0.2862 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9550 -0.2675 1.6447 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9164 1.0071 -0.5292 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3810 2.3529 -0.0996 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1238 2.3742 -0.1096 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7644 1.2342 0.6611 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5217 1.5939 2.1061 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1222 -0.0205 0.2162 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7765 -1.2341 0.8722 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1928 -1.2052 0.4030 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8529 -0.1101 0.2131 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2340 -0.1332 -0.2456 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7800 -1.5015 -0.5469 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0802 -1.2926 -1.2513 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7669 -0.8351 -2.6627 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7603 -2.6560 -1.3962 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0116 -0.3322 -0.6101 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4268 0.7577 0.1853 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1034 0.4455 0.8508 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5044 1.6198 1.5254 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0580 1.8299 1.5591 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2505 1.2062 0.4432 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5457 2.1358 -0.7607 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1486 2.7626 0.9793 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3837 -0.6216 1.8552 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5325 -1.0348 2.1514 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3393 -1.2321 2.5375 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5095 -2.2444 3.4999 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3718 1.0546 -0.7770 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2052 1.6758 0.3056 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5337 2.0003 -1.9926 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6775 -1.0392 -0.2992 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4026 0.1944 -0.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7405 -0.8329 -1.8237 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1666 -2.8484 -0.4026 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5799 -1.7497 0.8575 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7303 -2.5768 -0.4586 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5440 -2.0174 -2.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6192 -0.3245 0.3360 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3967 0.3485 -1.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0866 -0.3190 -2.3325 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7924 -1.9273 0.1468 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3666 -2.2738 -1.5220 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5882 -2.2450 0.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1540 -1.5177 -1.3855 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6284 -1.1476 1.7246 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5786 0.5839 1.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1283 -0.4894 2.3518 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4436 0.8679 -1.5569 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7229 2.7127 0.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7176 3.0795 -0.8679 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3720 3.3646 0.3370 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4256 2.2720 -1.1680 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5697 1.8375 2.2848 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0241 2.5485 2.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7825 0.8645 2.8471 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3488 -0.1506 -0.8608 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7131 -1.2058 1.9790 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3654 -2.1752 0.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7366 -2.1518 0.1987 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4201 0.4668 -1.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8050 -2.1769 0.2998 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0842 -1.9659 -1.3070 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8908 -1.3643 -3.0838 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6830 -1.1012 -3.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6850 0.2680 -2.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3013 -2.7202 -2.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5329 -2.7638 -0.6134 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0157 -3.4728 -1.3941 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6193 0.1532 -1.4336 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7901 -0.9318 -0.0537 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1470 1.0495 1.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2691 1.7019 -0.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9046 1.6185 2.5878 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8744 2.9273 1.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6752 1.4152 2.5142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1370 3.1165 -0.4854 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2348 1.7070 -1.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6662 2.3564 -0.7604 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1490 3.5029 1.6329 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5042 -2.4849 3.9068 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9368 -3.1650 3.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1227 -1.9238 4.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0846 2.2040 -0.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7261 2.4093 0.9368 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7130 0.9116 0.9609 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5974 3.0426 -1.6636 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4121 1.6850 -2.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6466 1.9137 -2.6590 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 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 6 30 34 1 0 29 35 1 1 35 36 2 0 35 37 1 0 37 38 1 0 13 39 1 0 39 40 1 0 39 41 1 0 39 8 1 0 18 11 1 0 32 21 1 0 32 16 1 0 29 22 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 2 46 1 0 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 8 51 1 6 9 52 1 0 9 53 1 0 10 54 1 0 10 55 1 0 12 56 1 0 12 57 1 0 12 58 1 0 13 59 1 6 14 60 1 0 14 61 1 0 15 62 1 0 15 63 1 0 17 64 1 0 17 65 1 0 17 66 1 0 18 67 1 6 19 68 1 0 19 69 1 0 20 70 1 0 22 71 1 6 23 72 1 0 23 73 1 0 25 74 1 0 25 75 1 0 25 76 1 0 26 77 1 0 26 78 1 0 26 79 1 0 27 80 1 0 27 81 1 0 28 82 1 0 28 83 1 0 30 84 1 1 31 85 1 0 31 86 1 0 33 87 1 0 33 88 1 0 33 89 1 0 34 90 1 0 38 91 1 0 38 92 1 0 38 93 1 0 40 94 1 0 40 95 1 0 40 96 1 0 41 97 1 0 41 98 1 0 41 99 1 0 M END

Standard InCHIKey	AOKGWENYNIEUGE-GHMKDZOHSA-N
Standard InCHI	InChI=1S/C36H58O5/c1-10-11-12-29(38)41-28-16-17-33(6)25(32(28,4)5)15-18-34(7)26(33)14-13-23-24-21-31(2,3)19-20-36(24,30(39)40-9)27(37)22-35(23,34)8/h13,24-28,37H,10-12,14-22H2,1-9H3/t24-,25+,26-,27-,28+,33+,34-,35-,36-/m1/s1
SMILES	CCCCC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@H]4CC(C)(C)CC[C@@]4([C@@H](C[C@@]32C)O)C(=O)OC)C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	570.43	Volume:	624.471 ? Van der Waals volume.
Dense:	0.913	LogP:	5.753 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.443 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.776 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	28.0
TPSA:	72.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.268	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.864	Fsp³:	0.889
MCE-18:	106.118 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.916	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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.382	Promiscuous compounds:	0.267

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.865	MDCK Permeability:	-4.633
Pgp-inhibitor:	0.982	Pgp-substrate:	0.005
PAMPA:	0.346 ? 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):	0.004
20% Bioavailability (F20%):	0.966	30% Bioavailability (F30%):	0.972
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.337	MRP1:	0.623
Plasma Protein Binding (PPB):	94.49%	Volume Distribution (VD):	0.174
Fu:	5.357% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.34
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.461	CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.995
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.085 ? 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):

8.673

Half-life (T1/2):

0.625

ADMET: Toxicity

hERG Blockers:	0.244	hERG Blockers (10um):	0.464
Human Hepatotoxicity (H-HT):	0.678	Drug-induced Liver Injury (DILI):	0.334
AMES Toxicity:	0.111	Rat Oral Acute Toxicity:	0.412
Maximum Recommended Daily Dose:	0.751	Skin Sensitization:	0.866
Carcinogencity:	0.866	Eye Corrosion:	0.011
Eye Irritation:	0.228	Respiratory Toxicity:	0.806
Drug-induced Neurotoxicity:	0.108	Ototoxicity:	0.484
Hematotoxicity:	0.316	Drug-induced Nephrotoxicity:	0.665
Genotoxicity:	0.112	RPMI-8226 Immunitoxicity:	0.056
A549 Cytotoxicity:	0.407	Hek293 Cytotoxicity:	0.551
BCF:	2.393 ? 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:	5.303 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.734 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.495 ? 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
NPO27443	Gymnocladus chinensis	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[7494144]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[7494144]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27443	Gymnocladus chinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7631	Gleditsia japonica	Species	Fabaceae	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
EC50	1
IC50	1

Activity Type	# Activity
Cell line	1
Organism	1

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
NPT759	Cell line	H9	Homo sapiens	IC50	=	180000.0	nM	PMID[7494144]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	30000.0	nM	PMID[7494144]

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 NPC488524 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	18350
0.1-0.2	25693
0.2-0.3	4784
0.3-0.4	835
0.4-0.5	160
0.5-0.6	22
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC488522
0.8806	High Similarity	NPC488520
0.7534	Intermediate Similarity	NPC86368
0.7123	Intermediate Similarity	NPC488525
0.7042	Intermediate Similarity	NPC488519
0.6667	Remote Similarity	NPC10005
0.6667	Remote Similarity	NPC91525
0.6622	Remote Similarity	NPC488523
0.6301	Remote Similarity	NPC162107
0.6301	Remote Similarity	NPC46912
0.618	Remote Similarity	NPC1046
0.6	Remote Similarity	NPC191965
0.5972	Remote Similarity	NPC195334
0.5938	Remote Similarity	NPC488526
0.589	Remote Similarity	NPC224145
0.5714	Remote Similarity	NPC286786
0.5612	Remote Similarity	NPC164389
0.5584	Remote Similarity	NPC9892
0.5584	Remote Similarity	NPC329943
0.557	Remote Similarity	NPC164349
0.5446	Remote Similarity	NPC64715
0.5325	Remote Similarity	NPC246708
0.5258	Remote Similarity	NPC480420
0.5256	Remote Similarity	NPC127855
0.5238	Remote Similarity	NPC104137
0.5238	Remote Similarity	NPC26626
0.5189	Remote Similarity	NPC11242
0.5185	Remote Similarity	NPC123522
0.5125	Remote Similarity	NPC481361
0.5119	Remote Similarity	NPC488518
0.5104	Remote Similarity	NPC475208
0.5065	Remote Similarity	NPC470588
0.5063	Remote Similarity	NPC137306
0.5053	Remote Similarity	NPC214484

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6831
0.1-0.2	2215
0.2-0.3	99
0.3-0.4	4
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