NPASS Compound

Natural Product: NPC4289

Natural Product ID	NPC4289
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QKKRBNPMUBNTPA-OQDRYOJTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

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 96 0 0 0 0 0 0 0 0999 V2000 -4.5601 2.1612 -4.3703 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9576 1.1938 -3.3717 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5130 1.5997 -2.2182 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9086 0.7605 -1.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4924 1.2248 -0.8913 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8255 0.4142 0.2375 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7192 0.6485 1.4388 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7665 -1.0020 -0.2034 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7432 -1.8791 0.5659 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6258 -3.3134 0.0957 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6232 -3.9735 -0.4678 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4315 -5.3945 -0.9126 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9637 -3.3555 -0.6796 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5629 -1.6841 -0.1594 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6866 -0.8850 -0.7721 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1066 -1.3996 -2.1186 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5318 -2.8127 -2.0135 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8599 -3.7726 -2.7011 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2341 -5.2090 -2.6346 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7136 -3.3900 -3.5666 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8050 -0.8523 0.1752 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7252 0.0197 1.2348 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9201 0.3182 1.9706 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9944 -0.3464 1.6478 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0814 1.2758 3.0280 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1772 2.2389 3.4106 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3818 3.1194 4.4802 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5624 3.0238 5.1995 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4984 2.0875 4.8639 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2477 1.2507 3.8104 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7113 1.9750 5.5857 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8099 3.8788 6.2700 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3532 0.4621 1.5115 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9691 0.3419 2.7080 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5313 1.0074 0.3967 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6411 2.4929 0.4649 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1322 3.1088 1.5524 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9092 4.1784 1.4468 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6163 4.6262 2.7030 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1318 5.0183 0.2568 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2257 0.5281 -0.8720 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3882 1.1855 -1.8334 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9330 -1.6398 0.0729 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9131 -0.2293 -3.7691 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8079 2.9298 -4.6743 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8772 1.6183 -5.2588 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4105 2.7009 -3.9033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5939 2.6792 -1.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5320 0.7973 -0.2500 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9024 -0.2733 -1.5559 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5689 2.2734 -0.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8908 1.0296 -1.7973 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2175 1.6472 1.3708 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2101 0.6056 2.3880 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5258 -0.1046 1.4743 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1157 -1.1178 -1.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8078 -1.6346 0.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5428 -1.8932 1.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6931 -3.8465 0.2356 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1787 -6.0579 -0.0707 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6157 -5.4677 -1.6616 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3587 -5.7829 -1.3888 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5757 -3.9969 -1.3458 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9369 -2.3679 -1.1391 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 -3.3003 0.3046 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4990 -2.6094 -0.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7655 -2.0033 0.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3762 -1.2377 -2.9098 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0392 -0.8094 -2.3777 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3536 -3.1990 -1.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2794 -5.3756 -2.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0075 -5.7395 -3.5799 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6257 -5.7447 -1.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2814 -4.2992 -4.0717 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1357 -2.9566 -3.0123 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0173 -2.6346 -4.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2818 2.3640 2.8381 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6303 3.8598 4.7429 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9978 0.5088 3.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5552 1.6491 6.5501 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4463 4.6525 6.2230 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7142 2.7487 0.5737 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3209 3.0001 -0.4736 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0670 2.6532 2.5620 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9949 5.6455 2.6257 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4882 3.9404 2.8171 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9453 4.4794 3.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2281 5.3103 0.1971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9372 4.4946 -0.6801 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5515 5.9736 0.3059 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9915 -2.3843 0.7878 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8936 -0.4747 -4.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2826 -0.8146 -2.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6005 -0.4369 -4.6320 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 6 5 1 6 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 3 11 12 1 0 11 13 1 0 8 14 1 0 14 15 1 0 15 16 1 6 16 17 1 0 17 18 2 3 18 19 1 0 18 20 1 0 15 21 1 0 21 22 2 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 29 31 1 0 28 32 1 0 22 33 1 0 33 34 2 0 33 35 1 0 35 36 1 6 36 37 1 0 37 38 2 3 38 39 1 0 38 40 1 0 35 41 1 0 41 42 2 0 21 43 1 0 2 44 1 0 35 6 1 0 41 15 1 0 30 25 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 0 5 52 1 0 7 53 1 0 7 54 1 0 7 55 1 0 8 56 1 6 9 57 1 0 9 58 1 0 10 59 1 0 12 60 1 0 12 61 1 0 12 62 1 0 13 63 1 0 13 64 1 0 13 65 1 0 14 66 1 0 14 67 1 0 16 68 1 0 16 69 1 0 17 70 1 0 19 71 1 0 19 72 1 0 19 73 1 0 20 74 1 0 20 75 1 0 20 76 1 0 26 77 1 0 27 78 1 0 30 79 1 0 31 80 1 0 32 81 1 0 36 82 1 0 36 83 1 0 37 84 1 0 39 85 1 0 39 86 1 0 39 87 1 0 40 88 1 0 40 89 1 0 40 90 1 0 43 91 1 0 44 92 1 0 44 93 1 0 44 94 1 0 M END

Standard InCHIKey	QKKRBNPMUBNTPA-OQDRYOJTSA-N
Standard InCHI	InChI=1S/C38H50O6/c1-23(2)11-10-18-36(9)28(14-12-24(3)4)22-37(19-16-25(5)6)33(42)31(32(41)27-13-15-29(39)30(40)21-27)34(43)38(36,35(37)44)20-17-26(7)8/h11-13,15-17,21,28,39-40,42H,10,14,18-20,22H2,1-9H3/t28-,36+,37-,38+/m1/s1
SMILES	CC(=CCC[C@@]1(C)[C@H](CC=C(C)C)C[C@]2(CC=C(C)C)C(=C(C(=O)c3ccc(c(c3)O)O)C(=O)[C@@]1(CC=C(C)C)C2=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.36	Volume:	663.875 ? Van der Waals volume.
Dense:	0.907	LogP:	6.952 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.158 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.746 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	111.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.077	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.577	Fsp³:	0.5
MCE-18:	98.439 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.993	Fluc inhibitor:	0.135 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.048 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.584 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.606	Promiscuous compounds:	0.204

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.786	MDCK Permeability:	-4.639
Pgp-inhibitor:	0.001	Pgp-substrate:	0.024
PAMPA:	0.991 ? 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%):	0.028	30% Bioavailability (F30%):	0.025
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097	MRP1:	0.974
Plasma Protein Binding (PPB):	89.063%	Volume Distribution (VD):	0.142
Fu:	12.204% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.834	BCRP inhibitor:	0.078
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.69
CYP2C19-inhibitor:	0.813	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.047	CYP2D6-substrate:	0.982
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.448
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.495
HLM stability:	0.999 ? 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):

6.893

Half-life (T1/2):

1.205

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.238
Human Hepatotoxicity (H-HT):	0.795	Drug-induced Liver Injury (DILI):	0.462
AMES Toxicity:	0.302	Rat Oral Acute Toxicity:	0.816
Maximum Recommended Daily Dose:	0.143	Skin Sensitization:	0.994
Carcinogencity:	0.512	Eye Corrosion:	0.0
Eye Irritation:	0.025	Respiratory Toxicity:	0.871
Drug-induced Neurotoxicity:	0.044	Ototoxicity:	0.93
Hematotoxicity:	0.458	Drug-induced Nephrotoxicity:	0.948
Genotoxicity:	0.994	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.84	Hek293 Cytotoxicity:	0.116
BCF:	1.863 ? 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:	5.805 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.896 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.781 ? 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
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4020(01)89039-6]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[16562837]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21028890]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	seeds and rinds	n.a.	n.a.	PMID[21028890]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	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
MIC	1

Activity Type	# Activity
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
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	15.0	ug.mL-1	PMID[32791400]

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 NPC4289 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	7170
0.1-0.2	40162
0.2-0.3	2355
0.3-0.4	91
0.4-0.5	32
0.5-0.6	6
0.6-0.7	17
0.7-0.8	0
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289358
1.0	High Similarity	NPC42384
0.9091	High Similarity	NPC5014
0.8939	High Similarity	NPC23667
0.8939	High Similarity	NPC157284
0.8485	Intermediate Similarity	NPC198803
0.8382	Intermediate Similarity	NPC482621
0.831	Intermediate Similarity	NPC482618
0.8194	Intermediate Similarity	NPC482617
0.8194	Intermediate Similarity	NPC482616
0.8125	Intermediate Similarity	NPC149773
0.7714	Intermediate Similarity	NPC165191
0.7714	Intermediate Similarity	NPC177501
0.7681	Intermediate Similarity	NPC48949
0.7639	Intermediate Similarity	NPC25736
0.7571	Intermediate Similarity	NPC114333
0.7571	Intermediate Similarity	NPC28592
0.7571	Intermediate Similarity	NPC51531
0.7465	Intermediate Similarity	NPC473479
0.7465	Intermediate Similarity	NPC50615
0.7465	Intermediate Similarity	NPC141650
0.7222	Intermediate Similarity	NPC30846
0.7042	Intermediate Similarity	NPC46242
0.7042	Intermediate Similarity	NPC91887
0.7042	Intermediate Similarity	NPC93556
0.6944	Remote Similarity	NPC297797
0.6757	Remote Similarity	NPC469857
0.6757	Remote Similarity	NPC245760
0.6579	Remote Similarity	NPC471971
0.6579	Remote Similarity	NPC471972
0.6579	Remote Similarity	NPC469855
0.6447	Remote Similarity	NPC294330
0.6282	Remote Similarity	NPC469856
0.6232	Remote Similarity	NPC259400
0.6232	Remote Similarity	NPC130591
0.6232	Remote Similarity	NPC234637
0.6203	Remote Similarity	NPC471970
0.6154	Remote Similarity	NPC469854
0.6154	Remote Similarity	NPC482619
0.6104	Remote Similarity	NPC479148
0.6027	Remote Similarity	NPC473779
0.6026	Remote Similarity	NPC479151
0.5833	Remote Similarity	NPC482620
0.575	Remote Similarity	NPC603871
0.5679	Remote Similarity	NPC237441
0.5616	Remote Similarity	NPC611064
0.5443	Remote Similarity	NPC473527
0.5422	Remote Similarity	NPC479146

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC4289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3582
0.1-0.2	5494
0.2-0.3	74
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