NPASS Compound

Natural Product: NPC480956

Natural Product ID	NPC480956
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PSIOAWBSHJERTA-BTUOBPCZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	122178981
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 94 98 0 0 0 0 0 0 0 0999 V2000 -8.9651 2.6632 -0.7136 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9632 1.8988 0.0672 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3344 1.2453 1.0988 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6382 1.8470 -0.2528 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6454 1.1128 0.4880 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6644 2.1148 0.9685 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3897 1.6298 1.5460 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9341 0.2848 0.9448 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3453 -0.7321 1.9251 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4446 0.3887 0.7590 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6925 0.7779 1.9702 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8029 0.6398 1.8141 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2511 0.6612 0.4058 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0316 2.0716 -0.1141 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6330 0.2593 0.0880 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5021 0.2590 -1.4718 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2063 -0.5407 -1.5347 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4774 -0.3257 -0.4627 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8322 -0.8194 0.0798 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5061 -1.8928 1.1430 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7341 -1.4667 -0.8901 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8372 -0.5953 -1.4230 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5257 0.2455 -0.4172 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0474 0.0804 -0.4218 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4945 -1.3124 -0.1647 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4362 0.4073 -1.8760 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1303 -2.0948 -1.9967 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2345 -3.4238 -2.3298 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9259 -4.1510 -1.5900 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5269 -3.9145 -3.5370 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7870 1.0866 0.4244 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0197 0.3247 -0.1937 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1813 0.9136 0.5560 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2428 -0.0915 0.9467 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0015 -0.6638 -0.2065 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1676 -1.6268 -1.0596 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6037 0.3462 -1.1286 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0639 -1.4823 0.2660 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1693 0.6417 1.7218 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5958 1.4631 1.7417 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2513 1.0387 1.8380 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7397 0.7370 2.9112 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4281 3.0914 -1.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3801 3.5121 -0.1408 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7445 1.9953 -1.1309 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2414 0.6442 1.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1790 2.7353 1.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5009 2.8520 0.1284 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4144 1.5769 2.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6246 2.4267 1.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0806 -1.7652 1.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4318 -0.6928 2.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8880 -0.4194 2.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3546 1.2135 -0.0027 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9721 0.2730 2.9133 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8936 1.8692 2.1855 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2382 -0.2232 2.3492 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2782 1.5473 2.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0137 2.5778 -0.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3933 2.6891 0.5509 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5571 2.0986 -1.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8729 -0.7945 0.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3866 1.2541 -1.8676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2655 -0.3588 -1.9300 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9075 -1.1984 -2.3362 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5808 -2.1909 1.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7281 -1.5795 2.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0620 -2.8350 0.9606 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2907 -2.3283 -0.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6160 -1.2760 -1.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4133 -0.0492 -2.3001 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4147 1.3077 -0.8188 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6422 -2.0259 -0.0285 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0765 -1.7615 -1.0258 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2253 -1.3897 0.6945 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4670 0.8068 -1.9163 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4530 -0.5521 -2.4625 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7304 1.1380 -2.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1919 -4.5793 -4.1559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2723 -3.0648 -4.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4261 -4.4233 -3.2853 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8889 2.0795 -0.0134 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0578 0.5720 -1.2721 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8724 -0.7243 0.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6042 1.7640 -0.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8671 -0.9028 1.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8790 -2.3098 -1.6225 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6162 -1.1044 -1.8624 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5591 -2.3096 -0.4586 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3638 -0.1964 -1.7584 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8737 0.7563 -1.8598 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1691 1.1383 -0.6067 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9032 -0.9345 0.3133 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6631 0.0655 2.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 21 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 15 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 34 39 1 0 33 40 1 0 40 41 1 0 41 42 2 0 24 5 1 0 41 31 1 0 23 8 1 0 19 10 1 0 18 13 1 0 1 43 1 0 1 44 1 0 1 45 1 0 5 46 1 1 6 47 1 0 6 48 1 0 7 49 1 0 7 50 1 0 9 51 1 0 9 52 1 0 9 53 1 0 10 54 1 6 11 55 1 0 11 56 1 0 12 57 1 0 12 58 1 0 14 59 1 0 14 60 1 0 14 61 1 0 15 62 1 1 16 63 1 0 16 64 1 0 17 65 1 0 20 66 1 0 20 67 1 0 20 68 1 0 21 69 1 1 22 70 1 0 22 71 1 0 23 72 1 6 25 73 1 0 25 74 1 0 25 75 1 0 26 76 1 0 26 77 1 0 26 78 1 0 30 79 1 0 30 80 1 0 30 81 1 0 31 82 1 6 32 83 1 0 32 84 1 0 33 85 1 6 34 86 1 1 36 87 1 0 36 88 1 0 36 89 1 0 37 90 1 0 37 91 1 0 37 92 1 0 38 93 1 0 39 94 1 0 M END

Standard InCHIKey	PSIOAWBSHJERTA-BTUOBPCZSA-N
Standard InCHI	InChI=1S/C34H52O8/c1-18(35)40-26-13-15-33(8)24-12-14-32(7)21(20-16-22(42-29(20)38)28(37)31(5,6)39)10-11-23(32)34(24,9)27(41-19(2)36)17-25(33)30(26,3)4/h11,20-22,24-28,37,39H,10,12-17H2,1-9H3/t20-,21-,22+,24+,25-,26+,27+,28-,32-,33+,34-/m0/s1
SMILES	CC(=O)O[C@@H]1CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC=C4[C@]3(C)[C@@H](C[C@H]2C1(C)C)OC(=O)C)[C@@H]1C[C@H]([C@@H](C(C)(C)O)O)OC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	588.37	Volume:	613.614 ? Van der Waals volume.
Dense:	0.959	LogP:	3.672 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.362 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.348 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	28.0
TPSA:	119.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.258	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.311	Fsp³:	0.853
MCE-18:	108.0 ? 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:	0.919	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.295	Promiscuous compounds:	0.517

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.068	MDCK Permeability:	-4.868
Pgp-inhibitor:	0.994	Pgp-substrate:	0.043
PAMPA:	0.472 ? 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%):	0.849	30% Bioavailability (F30%):	0.739
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.988
Plasma Protein Binding (PPB):	75.472%	Volume Distribution (VD):	-0.416
Fu:	15.273% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.182
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.984	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.037	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.422
CYP3A4-inhibitor:	0.041	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

7.169

Half-life (T1/2):

0.715

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.178
Human Hepatotoxicity (H-HT):	0.681	Drug-induced Liver Injury (DILI):	0.84
AMES Toxicity:	0.788	Rat Oral Acute Toxicity:	0.396
Maximum Recommended Daily Dose:	0.692	Skin Sensitization:	0.999
Carcinogencity:	0.894	Eye Corrosion:	0.001
Eye Irritation:	0.039	Respiratory Toxicity:	0.301
Drug-induced Neurotoxicity:	0.351	Ototoxicity:	0.571
Hematotoxicity:	0.835	Drug-induced Nephrotoxicity:	0.94
Genotoxicity:	0.992	RPMI-8226 Immunitoxicity:	0.105
A549 Cytotoxicity:	0.623	Hek293 Cytotoxicity:	0.755
BCF:	0.881 ? 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:	3.936 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.892 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.179 ? 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
NPO40807	Cameroonian entandrophragma	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25871440]

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	2
Ratio IC50	1

Activity Type	# Activity
Cell line	1
Organism	1
Others	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
NPT839	Cell line	L6	Rattus norvegicus	IC50	=	11000.0	nM	PMID[25871440]
NPT2258	Organism	Plasmodium falciparum NF54	Plasmodium falciparum NF54	IC50	=	870.0	nM	PMID[25871440]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	12.7	n.a.	PMID[25871440]

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 NPC480956 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	19164
0.1-0.2	23792
0.2-0.3	6551
0.3-0.4	307
0.4-0.5	31
0.5-0.6	9
0.6-0.7	2
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
0.8281	Intermediate Similarity	NPC480955
0.7143	Intermediate Similarity	NPC480952
0.6301	Remote Similarity	NPC470053
0.6081	Remote Similarity	NPC470066
0.5696	Remote Similarity	NPC470064
0.5696	Remote Similarity	NPC470043
0.5625	Remote Similarity	NPC470060
0.5625	Remote Similarity	NPC470059
0.5584	Remote Similarity	NPC480953
0.525	Remote Similarity	NPC5284
0.52	Remote Similarity	NPC472655
0.5128	Remote Similarity	NPC480954
0.5063	Remote Similarity	NPC470068

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6816
0.1-0.2	2226
0.2-0.3	106
0.3-0.4	2
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