NPASS Compound

Natural Product: NPC261659

Natural Product ID	NPC261659
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dichapetalin J
IUPAC Name	n.a.
Synonyms	Dichapetalin J
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL448039
PubChem CID	11549096
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 98105 0 0 0 0 0 0 0 0999 V2000 -9.0167 2.6415 -0.0301 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4710 1.2720 -0.4290 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8459 0.1792 -0.0136 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6734 0.2393 0.8602 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6952 -0.8832 0.6085 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3744 -0.2798 0.9709 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3046 -0.6560 -0.0444 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2098 -2.1652 -0.0307 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7784 -2.5315 0.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0216 -1.2400 0.4779 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4277 -0.5591 1.6900 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9414 -0.1332 0.3294 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4685 1.1302 -0.2894 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1671 1.0250 -1.0543 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2152 0.2696 -0.1697 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2248 0.4967 -0.4346 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6515 0.4871 -1.8604 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5274 1.9192 0.0884 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9961 2.1733 -0.0015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8357 1.2065 0.2133 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3054 1.4516 0.1239 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8013 0.6022 -1.0303 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2361 0.3456 -0.9037 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9750 0.9790 0.0596 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3461 0.7041 0.1561 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9723 -0.1839 -0.6894 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2232 -0.8100 -1.6476 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8773 -0.5433 -1.7457 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3490 -0.4512 -0.5822 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0756 0.2181 0.4197 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0219 -0.4886 -1.2746 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3828 -1.0771 -0.2226 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4536 -0.1905 0.5558 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8482 -0.3574 2.0321 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0111 -0.4671 0.4308 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6799 -1.8915 0.0394 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2403 -2.1224 0.4937 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6801 -1.1537 -0.1754 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8900 -1.6738 -1.6076 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2092 -1.9762 1.8668 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4381 1.5765 -1.1862 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5859 1.1631 1.0969 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8163 2.0438 1.5515 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8755 1.3866 0.5886 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6553 1.1075 -1.3166 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9132 -0.2216 -1.5682 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2018 3.0158 -0.6832 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7633 2.6882 1.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8766 3.3274 -0.1753 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2212 -0.7789 -0.3354 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9411 0.3177 1.9482 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9637 -1.7663 1.2230 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7782 -1.1547 -0.4657 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0865 -0.7439 1.9572 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5960 -0.3639 -1.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6348 -2.6163 -0.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8006 -2.6238 0.7931 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6162 -3.1836 1.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3704 -3.0737 -0.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1341 -1.0934 2.3881 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8003 0.1513 2.2668 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3112 1.9700 0.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8058 2.0323 -1.2578 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3469 0.5355 -2.0334 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4054 0.6549 0.8774 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5330 1.1871 -1.9813 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0240 -0.4812 -2.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8599 0.9413 -2.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0380 2.5999 -0.6358 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0996 2.0974 1.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3240 3.1510 -0.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5734 2.5138 0.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7084 1.1024 1.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6894 1.2736 -1.9360 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5800 1.6925 0.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9247 1.1995 0.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7092 -1.5037 -2.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3138 -1.0568 -2.5163 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8772 -0.1429 1.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1768 0.0619 0.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9181 1.3249 0.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8328 -1.9675 -0.6499 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1757 -1.5487 0.4184 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2586 -1.1904 2.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5051 0.5679 2.5430 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9149 -0.5532 2.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5383 -0.3355 1.4531 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3017 -2.6043 0.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7689 -2.0987 -1.0241 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0787 -3.1507 0.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9510 -1.5059 -1.9226 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2673 -1.1660 -2.3389 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6143 -2.7652 -1.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1150 -2.8876 2.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3404 2.5191 -1.4269 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5163 1.5692 -0.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4867 1.7048 -2.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6299 -0.4043 -2.5198 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 10 9 1 1 10 11 1 0 12 11 1 1 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 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 29 30 1 0 22 31 1 0 31 32 1 0 32 33 1 0 33 34 1 1 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 6 37 40 1 0 13 41 1 0 6 42 1 0 42 43 2 0 42 44 1 0 2 45 1 0 45 46 1 0 44 4 1 0 12 7 1 0 38 15 1 0 38 10 1 0 12 10 1 0 35 16 1 0 33 20 1 0 28 23 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 4 51 1 1 5 52 1 0 5 53 1 0 6 54 1 1 7 55 1 6 8 56 1 0 8 57 1 0 9 58 1 0 9 59 1 0 11 60 1 0 11 61 1 0 13 62 1 1 14 63 1 0 14 64 1 0 15 65 1 1 17 66 1 0 17 67 1 0 17 68 1 0 18 69 1 0 18 70 1 0 19 71 1 0 21 72 1 0 21 73 1 0 22 74 1 6 24 75 1 0 25 76 1 0 27 77 1 0 28 78 1 0 30 79 1 0 30 80 1 0 30 81 1 0 32 82 1 0 32 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 35 87 1 1 36 88 1 0 36 89 1 0 37 90 1 1 39 91 1 0 39 92 1 0 39 93 1 0 40 94 1 0 41 95 1 0 45 96 1 0 45 97 1 0 46 98 1 0 M END

Standard InCHIKey	KOTGYKATMONDCA-YZSQOBSSSA-N
Standard InCHI	InChI=1S/C39H52O7/c1-22(19-40)14-26-16-27(34(43)46-26)28-11-13-38-20-39(28,38)33(42)18-31-35(2)12-10-24-15-29(23-6-8-25(44-5)9-7-23)45-21-36(24,3)30(35)17-32(41)37(31,38)4/h6-10,14,26-33,40-42H,11-13,15-21H2,1-5H3/b22-14+/t26-,27-,28-,29-,30+,31+,32+,33+,35-,36-,37-,38+,39+/m0/s1
SMILES	C/C(=C[C@H]1C[C@@H]([C@@H]2CC[C@@]34C[C@]24[C@@H](C[C@@H]2[C@@]4(C)CC=C5C[C@@H](c6ccc(cc6)OC)OC[C@]5(C)[C@@H]4C[C@H]([C@@]32C)O)O)C(=O)O1)/CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	632.37	Volume:	660.361 ? Van der Waals volume.
Dense:	0.958	LogP:	2.935 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.069 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.72 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	40.0
TPSA:	105.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	8.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.273	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.81	Fsp³:	0.718
MCE-18:	190.149 ? 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:	0.904	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.05	Promiscuous compounds:	0.195

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.888	MDCK Permeability:	-4.68
Pgp-inhibitor:	0.56	Pgp-substrate:	0.452
PAMPA:	0.444 ? 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%):	0.408	30% Bioavailability (F30%):	0.432
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.809
Plasma Protein Binding (PPB):	93.563%	Volume Distribution (VD):	-0.079
Fu:	6.69% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.829
BSEP inhibitor:	0.964

ADMET: Metabolism

CYP1A2-inhibitor:	0.43	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.778	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.031	CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.985	CYP3A4-substrate:	0.908
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.177
HLM stability:	0.521 ? 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):

9.32

Half-life (T1/2):

1.291

ADMET: Toxicity

hERG Blockers:	0.13	hERG Blockers (10um):	0.206
Human Hepatotoxicity (H-HT):	0.968	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.889	Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.984	Skin Sensitization:	0.998
Carcinogencity:	0.918	Eye Corrosion:	0.0
Eye Irritation:	0.018	Respiratory Toxicity:	0.94
Drug-induced Neurotoxicity:	0.831	Ototoxicity:	0.721
Hematotoxicity:	0.578	Drug-induced Nephrotoxicity:	0.97
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.377
A549 Cytotoxicity:	0.984	Hek293 Cytotoxicity:	0.829
BCF:	1.107 ? 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:	3.726 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.448 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.698 ? 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
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	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
ED50	9

Activity Type	# Activity
Cell line	8
Non-molecular	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
NPT1034	Cell line	Lu1	Homo sapiens	ED50	=	14.5	ug ml-1	PMID[24480359]
NPT1851	Cell line	Col2	Homo sapiens	ED50	=	2.1	ug ml-1	PubChem BioAssay data set
NPT91	Cell line	KB	Homo sapiens	ED50	=	16.4	ug ml-1	PMID[18443109]
NPT91	Cell line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[12646019]
NPT858	Cell line	LNCaP	Homo sapiens	ED50	=	16.4	ug ml-1	PMID[14518939]
NPT2345	Cell line	SW626	Homo sapiens	ED50	=	0.4	ug ml-1	PubChem BioAssay data set
NPT136	Cell line	SK-N-SH	Homo sapiens	ED50	=	4.0	ug ml-1	PMID[21078949]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[16562829]

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 NPC261659 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	7560
0.1-0.2	39708
0.2-0.3	2557
0.3-0.4	15
0.4-0.5	12
0.5-0.6	1
0.6-0.7	1
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
0.8736	High Similarity	NPC79921
0.8065	Intermediate Similarity	NPC253591
0.7263	Intermediate Similarity	NPC262324
0.701	Intermediate Similarity	NPC243893
0.6364	Remote Similarity	NPC471864
0.5714	Remote Similarity	NPC601361

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC261659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3347
0.1-0.2	5728
0.2-0.3	75
0.3-0.4	0
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