NPASS Compound

Natural Product: NPC488214

Natural Product ID	NPC488214
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BZLJCXKYDLNUMS-CAQHHSHESA-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 99104 0 0 0 0 0 0 0 0999 V2000 3.7818 2.1785 1.3137 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0527 0.8533 1.2166 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3624 0.0850 2.5084 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5774 1.0496 1.0702 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9817 -0.0705 0.2289 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4935 -0.0600 0.3470 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0096 -0.5378 1.4635 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4384 -0.6218 1.7898 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2985 -0.1057 0.6964 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7515 -0.4405 0.8195 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9480 -1.8905 1.1256 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2780 0.3476 2.0113 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4753 1.1655 1.7207 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5137 0.4833 0.8728 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9369 -0.0624 -0.4122 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4062 0.9014 -1.5217 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5102 -1.4038 -0.7717 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4561 0.0219 -0.4162 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8848 -0.6013 -1.6724 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4968 -0.0275 -1.8201 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6698 -0.3957 -0.6428 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2384 -1.8353 -0.7768 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4173 0.4543 -0.6892 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7170 1.8998 -0.3183 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7947 0.4796 -2.0592 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6646 0.8394 -2.0199 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4966 -0.0582 -1.1581 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9198 0.4925 -1.1801 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6529 0.0838 0.0580 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0131 0.4682 -0.0595 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0590 -0.4301 0.0591 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8051 -1.6369 0.2796 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4648 -0.0397 -0.0611 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4322 -0.9082 0.0556 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8151 -0.5549 -0.0572 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2085 0.7322 -0.2986 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5662 1.0552 -0.4045 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5452 0.0962 -0.2705 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1395 -1.2075 -0.0257 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8105 -1.5202 0.0774 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5684 -1.4315 -1.7148 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9859 -1.7959 -2.7763 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3069 -2.3870 -1.0563 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1967 -0.5173 1.6013 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1811 2.4249 1.1810 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2079 2.3452 2.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6216 2.2331 0.5924 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0970 3.0128 1.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4529 -0.1021 2.4943 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7914 -0.8526 2.5542 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1409 0.7122 3.3790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1002 1.0000 2.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3368 2.0460 0.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3508 -1.0204 0.7150 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3276 -0.9203 2.2505 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6312 -0.0291 2.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6291 -1.6712 2.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2688 1.0247 0.7901 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6145 -2.0513 2.1940 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5106 -2.5924 0.4209 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0390 -2.1617 1.1806 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5008 1.0312 2.4440 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5335 -0.3374 2.8730 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9790 1.3857 2.7071 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3074 1.2609 0.6835 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4515 0.3444 -2.4790 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7585 1.7933 -1.5558 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4586 1.1494 -1.2538 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7875 -2.1509 -1.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1372 -1.7328 0.1097 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2724 -1.3463 -1.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2002 1.1227 -0.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4953 -0.2445 -2.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8839 -1.6984 -1.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0531 -0.5001 -2.7193 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5859 1.0413 -2.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9397 -2.4449 -1.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1426 -2.3429 0.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2456 -1.9532 -1.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6681 2.2710 -0.6893 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5403 2.0802 0.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9321 2.5303 -0.8076 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9124 -0.4463 -2.6185 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3095 1.2780 -2.6337 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0251 0.8583 -3.0710 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7879 1.8699 -1.6485 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9530 1.5780 -1.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4247 0.0781 -2.0819 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6565 -1.0087 0.2477 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6668 0.9835 -0.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1748 -1.9592 0.2491 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5403 1.5606 -0.4208 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8650 2.0754 -0.5954 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5953 0.3670 -0.3564 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9319 -1.9538 0.0776 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5387 -2.5416 0.2679 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1777 -3.3804 -1.1192 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8232 -0.1000 2.2332 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5954 2.9370 1.7913 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 1 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 6 41 42 2 0 41 43 1 0 14 44 1 0 13 45 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 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 1 7 55 1 0 8 56 1 0 8 57 1 0 9 58 1 1 11 59 1 0 11 60 1 0 11 61 1 0 12 62 1 0 12 63 1 0 13 64 1 1 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 45 99 1 0 M END

Standard InCHIKey	BZLJCXKYDLNUMS-CAQHHSHESA-N
Standard InCHI	InChI=1S/C39H54O6/c1-34(2)21-26-25-14-15-29-36(5)22-27(40)32(42)35(3,4)28(36)17-18-38(29,7)37(25,6)19-20-39(26,33(43)44)23-30(34)45-31(41)16-13-24-11-9-8-10-12-24/h8-14,16,26-30,32,40,42H,15,17-23H2,1-7H3,(H,43,44)/b16-13+/t26-,27+,28-,29+,30+,32-,36-,37+,38+,39+/m0/s1
SMILES	CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)C[C@H]([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)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.39	Volume:	666.047 ? Van der Waals volume.
Dense:	0.928	LogP:	4.416 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.91 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.213 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	35.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.184	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.047	Fsp³:	0.692
MCE-18:	165.879 ? 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:	0.986	Fluc inhibitor:	0.668 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.132 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.028 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.095	Promiscuous compounds:	0.037

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.49	MDCK Permeability:	-5.084
Pgp-inhibitor:	0.527	Pgp-substrate:	0.019
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):	0.001
20% Bioavailability (F20%):	0.498	30% Bioavailability (F30%):	0.459
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062	MRP1:	0.833
Plasma Protein Binding (PPB):	95.876%	Volume Distribution (VD):	-0.302
Fu:	3.368% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.954	BCRP inhibitor:	0.004
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.996
CYP2C9-inhibitor:	0.019	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.005 ? 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):

1.875

Half-life (T1/2):

1.409

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.03
Human Hepatotoxicity (H-HT):	0.56	Drug-induced Liver Injury (DILI):	0.74
AMES Toxicity:	0.254	Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.563	Skin Sensitization:	0.956
Carcinogencity:	0.553	Eye Corrosion:	0.003
Eye Irritation:	0.166	Respiratory Toxicity:	0.391
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.717
Hematotoxicity:	0.3	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.33	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.099	Hek293 Cytotoxicity:	0.119
BCF:	1.131 ? 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:	4.345 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.172 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.484 ? 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	=	11300.0	nM	PMID[29394063]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	6900.0	nM	PMID[29394063]
NPT2	Others	Unspecified	n.a.	Ratio CC50/IC50	>	9.0	n.a.	PMID[29394063]
NPT2	Others	Unspecified	n.a.	Ratio CC50/IC50	>	14.0	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 NPC488214 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	10353
0.1-0.2	34380
0.2-0.3	4424
0.3-0.4	475
0.4-0.5	163
0.5-0.6	56
0.6-0.7	5
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	NPC488215
0.6737	Remote Similarity	NPC171007
0.6737	Remote Similarity	NPC190849
0.6228	Remote Similarity	NPC488211
0.604	Remote Similarity	NPC605663
0.6	Remote Similarity	NPC22676
0.598	Remote Similarity	NPC132126
0.5979	Remote Similarity	NPC485587
0.5966	Remote Similarity	NPC111466
0.593	Remote Similarity	NPC84319
0.593	Remote Similarity	NPC52021
0.593	Remote Similarity	NPC599947
0.5887	Remote Similarity	NPC488210
0.5862	Remote Similarity	NPC472149
0.582	Remote Similarity	NPC488212
0.5648	Remote Similarity	NPC601567
0.5648	Remote Similarity	NPC606631
0.5619	Remote Similarity	NPC479747
0.5619	Remote Similarity	NPC479746
0.5619	Remote Similarity	NPC482049
0.5619	Remote Similarity	NPC482050
0.5607	Remote Similarity	NPC479740
0.5607	Remote Similarity	NPC479741
0.5577	Remote Similarity	NPC482052
0.5566	Remote Similarity	NPC610795
0.5524	Remote Similarity	NPC304110
0.5524	Remote Similarity	NPC25491
0.5524	Remote Similarity	NPC27518
0.5524	Remote Similarity	NPC611516
0.5481	Remote Similarity	NPC198621
0.5481	Remote Similarity	NPC216940
0.5472	Remote Similarity	NPC178093
0.5444	Remote Similarity	NPC259733
0.5444	Remote Similarity	NPC158371
0.5444	Remote Similarity	NPC207922
0.5429	Remote Similarity	NPC172311
0.5421	Remote Similarity	NPC482051
0.5421	Remote Similarity	NPC324798
0.5421	Remote Similarity	NPC479742
0.537	Remote Similarity	NPC479745
0.5333	Remote Similarity	NPC71074
0.5333	Remote Similarity	NPC37221
0.5333	Remote Similarity	NPC110308
0.5333	Remote Similarity	NPC605937
0.5326	Remote Similarity	NPC25299
0.5326	Remote Similarity	NPC481322
0.5299	Remote Similarity	NPC40085
0.5294	Remote Similarity	NPC173569
0.5283	Remote Similarity	NPC479744
0.5221	Remote Similarity	NPC264270
0.5208	Remote Similarity	NPC188833
0.5185	Remote Similarity	NPC479739
0.5179	Remote Similarity	NPC481234
0.5179	Remote Similarity	NPC118033
0.5179	Remote Similarity	NPC479431
0.5165	Remote Similarity	NPC231063
0.5165	Remote Similarity	NPC282395
0.5165	Remote Similarity	NPC609452
0.5048	Remote Similarity	NPC477874
0.5047	Remote Similarity	NPC262970
0.5038	Remote Similarity	NPC120667
0.5038	Remote Similarity	NPC278272

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488214 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3152
0.1-0.2	5872
0.2-0.3	122
0.3-0.4	3
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