NPASS Compound

Natural Product: NPC266511

Natural Product ID	NPC266511
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Balsaminol B
IUPAC Name	(3S,4S,7S,8R,9S,10S,13R,14S,17R)-4-(hydroxymethyl)-17-[(2R,4R)-4-hydroxy-6-methylhept-5-en-2-yl]-7-methoxy-4,9,13,14-tetramethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms	Balsaminol B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1078437
PubChem CID	44607277
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

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 87 90 0 0 0 0 0 0 0 0999 V2000 -2.5092 3.0464 2.4201 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8789 2.4460 1.2432 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4591 1.1045 1.1376 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5915 0.1824 1.2234 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0814 -0.3822 0.1909 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5096 -0.1186 -1.1364 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0773 0.2676 -1.2051 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5360 0.9676 -0.0315 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2494 0.4052 0.5251 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4619 -0.7801 1.3975 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5104 1.3495 1.4095 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8642 0.6500 1.4742 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9774 -0.2505 0.2652 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8185 0.2491 -0.5362 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2624 -0.6376 -1.5702 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1857 -0.9544 -1.4872 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2718 1.6064 -1.0189 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3388 -0.0587 -0.4212 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3653 -0.4117 0.6169 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7826 -0.2935 0.1689 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7356 -0.6618 1.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0274 -0.5012 1.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5405 0.0086 -0.2500 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0416 -0.8423 2.0837 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0594 0.9840 -0.2699 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4604 -1.0638 -1.5475 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0034 1.0436 -2.5135 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4997 0.8431 -1.7520 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8207 0.1204 -1.8485 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8482 -1.2581 -1.2875 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2614 -1.3236 0.1367 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7214 -2.7152 0.3507 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3329 -1.0376 1.0896 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9095 0.2393 0.9329 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1877 -1.6380 -1.1626 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9104 4.1005 2.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9883 2.5793 3.3064 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4224 3.1751 2.5543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9112 0.9396 2.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0119 -0.0066 2.2012 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5754 -1.0809 -1.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2744 2.0149 -0.3679 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0348 -0.6834 2.3860 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5130 -1.1127 1.4846 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0651 -1.6855 0.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1087 1.3335 2.4697 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5251 2.3775 1.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9891 0.0905 2.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6471 1.4397 1.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9936 -1.3134 0.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5373 -0.2500 -2.5965 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7970 -1.6193 -1.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5004 -1.3007 -2.5192 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4595 -1.8008 -0.8380 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8287 1.4014 -1.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9253 2.1338 -0.3155 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4852 2.3061 -1.2879 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4634 0.9275 -0.8589 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2531 0.1727 1.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1603 -1.4801 0.9232 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0086 -1.0668 -0.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4206 -1.0344 2.2289 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9740 -0.3757 -1.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5210 1.1226 -0.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5953 -0.2906 -0.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6703 0.0618 2.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5481 -1.0678 3.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6973 -1.6516 1.7163 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5408 1.6217 0.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3493 -2.0991 -1.2202 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8378 -0.7970 -2.4310 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5138 -0.9664 -1.9484 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9369 1.1178 -2.8827 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3382 2.0779 -2.4221 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4560 0.4576 -3.3387 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6788 1.7243 -1.0637 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1880 1.2955 -2.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0129 0.0072 -2.9582 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6615 0.7561 -1.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3777 -2.0176 -1.9430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0676 -2.7603 1.2437 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6170 -3.3707 0.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1906 -3.0982 -0.5442 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1725 -1.7448 0.8694 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1028 -1.1848 2.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2401 0.9589 1.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8144 -0.9192 -1.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 1 6 13 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 3 22 23 1 0 22 24 1 0 20 25 1 0 18 26 1 0 7 27 1 6 6 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 1 31 33 1 0 33 34 1 0 30 35 1 0 8 3 1 0 14 9 1 0 31 5 1 0 16 7 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 1 4 40 1 0 6 41 1 6 8 42 1 6 10 43 1 0 10 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 13 50 1 1 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 17 57 1 0 18 58 1 6 19 59 1 0 19 60 1 0 20 61 1 6 21 62 1 0 23 63 1 0 23 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 26 72 1 0 27 73 1 0 27 74 1 0 27 75 1 0 28 76 1 0 28 77 1 0 29 78 1 0 29 79 1 0 30 80 1 6 32 81 1 0 32 82 1 0 32 83 1 0 33 84 1 0 33 85 1 0 34 86 1 0 35 87 1 0 M END

Standard InCHIKey	XIQPIAMRFKEZPL-IQOYCCEYSA-N
Standard InCHI	InChI=1S/C31H52O4/c1-19(2)15-21(33)16-20(3)22-11-12-31(7)27-25(35-8)17-24-23(9-10-26(34)29(24,5)18-32)28(27,4)13-14-30(22,31)6/h15,17,20-23,25-27,32-34H,9-14,16,18H2,1-8H3/t20-,21+,22-,23-,25+,26+,27-,28+,29-,30-,31+/m1/s1
SMILES	CO[C@H]1C=C2[C@H]([C@]3([C@@H]1[C@]1(C)CC[C@@H]([C@]1(CC3)C)[C@@H](C[C@H](C=C(C)C)O)C)C)CC[C@@H]([C@]2(C)CO)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.39	Volume:	540.394 ? Van der Waals volume.
Dense:	0.904	LogP:	5.081 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.331 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.546 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	21.0
TPSA:	69.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.407	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.336	Fsp³:	0.871
MCE-18:	83.069 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.72	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? 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:	0.367	Promiscuous compounds:	0.354

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.253	MDCK Permeability:	-4.911
Pgp-inhibitor:	0.814	Pgp-substrate:	0.243
PAMPA:	0.829 ? 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):	0.004
20% Bioavailability (F20%):	0.967	30% Bioavailability (F30%):	0.865
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.969	MRP1:	0.779
Plasma Protein Binding (PPB):	77.819%	Volume Distribution (VD):	-0.208
Fu:	20.597% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.975	BCRP inhibitor:	0.913
BSEP inhibitor:	0.972

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.817 ? 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):

12.208

Half-life (T1/2):

1.449

ADMET: Toxicity

hERG Blockers:	0.118	hERG Blockers (10um):	0.314
Human Hepatotoxicity (H-HT):	0.7	Drug-induced Liver Injury (DILI):	0.143
AMES Toxicity:	0.387	Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.714	Skin Sensitization:	0.996
Carcinogencity:	0.878	Eye Corrosion:	0.0
Eye Irritation:	0.522	Respiratory Toxicity:	0.772
Drug-induced Neurotoxicity:	0.13	Ototoxicity:	0.82
Hematotoxicity:	0.417	Drug-induced Nephrotoxicity:	0.878
Genotoxicity:	0.738	RPMI-8226 Immunitoxicity:	0.144
A549 Cytotoxicity:	0.727	Hek293 Cytotoxicity:	0.676
BCF:	2.111 ? 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:	4.014 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.376 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.777 ? 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
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	African	n.a.	PMID[19795842]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20541427]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31339732]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	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
Activity	4
Flu intensity	2
Ratio	2
CI	1
IC50	6
Inhibition	1

Activity Type	# Activity
Cell line	2
Organism	3
Individual protein	9
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	258.8	n.a.	PMID[27591010]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	461.8	n.a.	PMID[27591010]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	439.5	n.a.	PMID[27591010]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	260.7	n.a.	PMID[27591010]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	95.7	n.a.	PMID[27591010]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	899.1	n.a.	PMID[27591010]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	7.3	n.a.	PMID[27591010]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	68.7	n.a.	PMID[27591010]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	CI	=	0.378	n.a.	PMID[27591010]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	55300.0	nM	DrugMatrix in vitro pharmacology data
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	31000.0	nM	PMID[18025117]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	17900.0	nM	Open TG-GATES in vivo data: Biochemistry
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	15200.0	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	31000.0	nM	PMID[27591010]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	7700.0	nM	PMID[27591010]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	47.0	%	PMID[17958396]

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 NPC266511 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	17645
0.1-0.2	27781
0.2-0.3	4292
0.3-0.4	113
0.4-0.5	13
0.5-0.6	8
0.6-0.7	3
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	Natural Product ID
0.6885	Remote Similarity	NPC101462
0.6364	Remote Similarity	NPC274448
0.6176	Remote Similarity	NPC157257
0.5672	Remote Similarity	NPC48010
0.5441	Remote Similarity	NPC185568
0.5352	Remote Similarity	NPC149224
0.5224	Remote Similarity	NPC31985
0.5143	Remote Similarity	NPC1015
0.5125	Remote Similarity	NPC93352
0.5072	Remote Similarity	NPC205845
0.5068	Remote Similarity	NPC177641

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC266511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6811
0.1-0.2	2245
0.2-0.3	93
0.3-0.4	1
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