NPASS Compound

Natural Product: NPC488215

Natural Product ID	NPC488215
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ORVHJQXVUAOELM-IJODRZMISA-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]

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 98103 0 0 0 0 0 0 0 0999 V2000 3.3245 1.7166 -1.6208 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5819 1.6096 -0.2982 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4359 2.9823 0.3058 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2326 0.9617 -0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7157 0.5159 0.7521 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7206 0.2186 0.8365 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4825 1.1981 1.2338 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9496 1.0872 1.3800 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3758 0.1587 0.2633 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7762 0.3464 -0.1604 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7561 0.5361 0.9435 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8307 1.6710 -0.9620 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2655 1.9356 -1.2788 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9761 0.8566 -2.0212 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4136 -0.5155 -1.8951 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2179 -1.0294 -3.3415 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4842 -1.4539 -1.3464 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1195 -0.6476 -1.2097 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8552 -2.0186 -0.6444 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3389 -2.1986 -0.4581 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8187 -1.1716 0.5708 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2604 -1.8030 1.8760 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3127 -1.0864 0.5090 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8045 -1.6319 -0.8232 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6520 -2.0250 1.5273 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8066 -1.8746 1.6125 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4748 -0.5833 1.4133 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8061 -0.7130 0.6496 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3913 0.6722 0.5858 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7198 0.5487 0.1151 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8509 0.9343 0.8046 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6702 1.4404 1.9569 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2039 0.7691 0.2349 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2712 1.1393 0.8917 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5978 0.9745 0.3264 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7805 0.4297 -0.8947 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0744 0.2949 -1.3978 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1895 0.6934 -0.7062 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0063 1.2549 0.5516 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7315 1.3861 1.0445 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9691 -0.1529 2.7882 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7233 0.9763 3.2550 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7081 -1.0424 3.5310 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3260 0.8920 -1.5864 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8397 2.6891 -1.7271 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1114 0.9272 -1.7085 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6227 1.5401 -2.4816 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0119 3.7032 -0.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6335 3.0098 1.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3540 3.2681 0.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4338 0.2416 -1.3383 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5130 1.7026 -0.9740 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9428 1.4400 1.3918 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0752 2.1961 1.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1439 0.7118 2.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4658 2.0663 1.3342 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7843 0.4953 -0.6513 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6058 -0.0435 1.8515 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6564 1.6125 1.2868 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7919 0.4257 0.6402 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2667 1.5327 -1.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4314 2.5056 -0.4031 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8032 2.2159 -0.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2793 2.9131 -1.8528 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0534 1.2102 -3.0946 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1706 -1.2938 -3.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7428 -0.2059 -3.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4812 -1.8542 -3.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3287 -1.7088 -0.2835 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4663 -2.4557 -1.8688 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4779 -1.0230 -1.5638 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3027 -0.5151 -1.9924 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1147 -2.7447 -1.4610 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4406 -2.2969 0.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9010 -2.0438 -1.4574 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2855 -3.2362 -0.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0243 -1.2650 2.7750 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8001 -2.8424 1.8515 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3412 -2.0428 1.8892 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1092 -2.6947 -0.9173 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1372 -1.1027 -1.6969 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3205 -1.7511 -0.7519 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0817 -1.8718 2.5379 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8819 -3.0828 1.2689 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2646 -2.5835 0.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1518 -2.3360 2.5739 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6623 -1.1799 -0.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4584 -1.3143 1.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3466 1.1115 1.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2655 0.3352 -0.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1521 1.5862 1.8963 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0044 0.0760 -1.5434 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2334 -0.1398 -2.3746 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1933 0.5812 -1.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8912 1.5651 1.0865 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5961 1.8216 2.0190 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3505 -0.7389 4.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4375 1.4418 -0.7835 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 27 41 1 1 41 42 2 0 41 43 1 0 14 44 1 0 29 2 1 0 40 35 1 0 27 5 1 0 23 6 1 0 21 9 1 0 18 10 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 1 7 54 1 0 8 55 1 0 8 56 1 0 9 57 1 6 11 58 1 0 11 59 1 0 11 60 1 0 12 61 1 0 12 62 1 0 13 63 1 0 13 64 1 0 14 65 1 6 16 66 1 0 16 67 1 0 16 68 1 0 17 69 1 0 17 70 1 0 17 71 1 0 18 72 1 6 19 73 1 0 19 74 1 0 20 75 1 0 20 76 1 0 22 77 1 0 22 78 1 0 22 79 1 0 24 80 1 0 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 26 85 1 0 26 86 1 0 28 87 1 0 28 88 1 0 29 89 1 1 33 90 1 0 34 91 1 0 36 92 1 0 37 93 1 0 38 94 1 0 39 95 1 0 40 96 1 0 43 97 1 0 44 98 1 0 M END

Standard InCHIKey	ORVHJQXVUAOELM-IJODRZMISA-N
Standard InCHI	InChI=1S/C39H54O5/c1-34(2)23-27-26-14-15-29-36(5)19-18-30(40)35(3,4)28(36)17-20-38(29,7)37(26,6)21-22-39(27,33(42)43)24-31(34)44-32(41)16-13-25-11-9-8-10-12-25/h8-14,16,27-31,40H,15,17-24H2,1-7H3,(H,42,43)/b16-13+/t27-,28-,29+,30-,31+,36-,37+,38+,39+/m0/s1
SMILES	CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@]2(C[C@H]1OC(=O)/C=C/c1ccccc1)C(=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.4	Volume:	657.257 ? Van der Waals volume.
Dense:	0.917	LogP:	5.407 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.278 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.214 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	35.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.205	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.88	Fsp³:	0.692
MCE-18:	162.273 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.976	Fluc inhibitor:	0.697 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.117 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.032 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.108	Promiscuous compounds:	0.026

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.512	MDCK Permeability:	-5.115
Pgp-inhibitor:	0.756	Pgp-substrate:	0.017
PAMPA:	0.999 ? 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%):	0.651	30% Bioavailability (F30%):	0.249
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102	MRP1:	0.895
Plasma Protein Binding (PPB):	97.029%	Volume Distribution (VD):	-0.449
Fu:	2.767% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.882	BCRP inhibitor:	0.012
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.999
CYP2C9-inhibitor:	0.302	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

2.656

Half-life (T1/2):

1.103

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.039
Human Hepatotoxicity (H-HT):	0.605	Drug-induced Liver Injury (DILI):	0.724
AMES Toxicity:	0.319	Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.79	Skin Sensitization:	0.989
Carcinogencity:	0.772	Eye Corrosion:	0.009
Eye Irritation:	0.224	Respiratory Toxicity:	0.784
Drug-induced Neurotoxicity:	0.035	Ototoxicity:	0.524
Hematotoxicity:	0.325	Drug-induced Nephrotoxicity:	0.974
Genotoxicity:	0.68	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.35	Hek293 Cytotoxicity:	0.289
BCF:	1.383 ? 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:	4.548 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.282 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.683 ? 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
NPO28138	Burkea africana	Species	Fabaceae	Eukaryota	Bark	n.a.	n.a.	PMID[29394063]
NPO28138	Burkea africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28138	Burkea africana	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
IC50	2
Ratio CC50/IC50	2
CC50	1

Activity Type	# Activity
Cell line	1
Organism	2
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
NPT616	Cell line	MDCK	Canis lupus familiaris	CC50	>	100000.0	nM	PMID[29394063]
NPT339	Organism	Influenza A virus H3N2	Influenza A virus H3N2	IC50	=	8900.0	nM	PMID[29394063]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	6800.0	nM	PMID[29394063]
NPT2	Others	Unspecified	n.a.	Ratio CC50/IC50	>	11.0	n.a.	PMID[29394063]
NPT2	Others	Unspecified	n.a.	Ratio CC50/IC50	>	15.0	n.a.	PMID[29394063]

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 NPC488215 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	9741
0.1-0.2	34045
0.2-0.3	5133
0.3-0.4	673
0.4-0.5	186
0.5-0.6	56
0.6-0.7	10
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
0.8391	Intermediate Similarity	NPC488214
0.6636	Remote Similarity	NPC488211
0.6526	Remote Similarity	NPC171007
0.6526	Remote Similarity	NPC190849
0.6348	Remote Similarity	NPC111466
0.6289	Remote Similarity	NPC22676
0.6277	Remote Similarity	NPC485587
0.6224	Remote Similarity	NPC198621
0.6224	Remote Similarity	NPC216940
0.6186	Remote Similarity	NPC488212
0.61	Remote Similarity	NPC132126
0.5952	Remote Similarity	NPC480946
0.5952	Remote Similarity	NPC130577
0.5952	Remote Similarity	NPC142415
0.5952	Remote Similarity	NPC102683
0.59	Remote Similarity	NPC262970
0.5882	Remote Similarity	NPC182797
0.5882	Remote Similarity	NPC52169
0.5882	Remote Similarity	NPC488562
0.5854	Remote Similarity	NPC488210
0.5842	Remote Similarity	NPC605663
0.5825	Remote Similarity	NPC610795
0.5686	Remote Similarity	NPC172311
0.5686	Remote Similarity	NPC482052
0.5615	Remote Similarity	NPC40085
0.5556	Remote Similarity	NPC173569
0.5534	Remote Similarity	NPC54627
0.5534	Remote Similarity	NPC249817
0.553	Remote Similarity	NPC264270
0.5514	Remote Similarity	NPC206232
0.5514	Remote Similarity	NPC14515
0.5463	Remote Similarity	NPC601567
0.5463	Remote Similarity	NPC606631
0.5402	Remote Similarity	NPC187722
0.5393	Remote Similarity	NPC202728
0.5393	Remote Similarity	NPC158059
0.5385	Remote Similarity	NPC479744
0.5368	Remote Similarity	NPC603645
0.5341	Remote Similarity	NPC51700
0.5341	Remote Similarity	NPC88716
0.5341	Remote Similarity	NPC68160
0.5341	Remote Similarity	NPC606443
0.5333	Remote Similarity	NPC304110
0.5333	Remote Similarity	NPC25491
0.5333	Remote Similarity	NPC27518
0.5333	Remote Similarity	NPC611516
0.5294	Remote Similarity	NPC475627
0.5294	Remote Similarity	NPC477874
0.5283	Remote Similarity	NPC479739
0.5283	Remote Similarity	NPC178093
0.5234	Remote Similarity	NPC482051
0.5234	Remote Similarity	NPC324798
0.5234	Remote Similarity	NPC479742
0.5222	Remote Similarity	NPC293564
0.5222	Remote Similarity	NPC298554
0.5196	Remote Similarity	NPC18982
0.5192	Remote Similarity	NPC477873
0.5185	Remote Similarity	NPC479745
0.5182	Remote Similarity	NPC310729
0.5182	Remote Similarity	NPC150310
0.5169	Remote Similarity	NPC270768
0.5169	Remote Similarity	NPC59263
0.5169	Remote Similarity	NPC210106
0.5169	Remote Similarity	NPC121798
0.5169	Remote Similarity	NPC234346
0.5093	Remote Similarity	NPC475311
0.5056	Remote Similarity	NPC198664

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3082
0.1-0.2	5909
0.2-0.3	152
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