NPASS Compound

Natural Product: NPC481421

Natural Product ID	NPC481421
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CNASGYYQUHJFQY-NFZOLUOBSA-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:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 96102 0 0 0 0 0 0 0 0999 V2000 8.1550 -2.0611 -2.8434 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2870 -2.1521 -1.6098 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8738 -2.4256 -2.0331 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0794 -1.1404 -1.8679 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1075 -0.7884 -0.4157 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2682 0.4548 -0.1055 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6636 1.6405 -0.9072 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8900 -0.0825 -0.4463 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0431 -1.5324 0.0295 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1579 -1.5545 1.2880 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0379 -0.7050 0.8284 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0444 -0.2455 1.8039 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5078 -1.3278 2.6827 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2884 -0.5622 3.7651 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4688 0.0087 3.0713 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3876 0.6353 4.0631 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5490 1.3602 3.4914 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3729 1.9002 2.1064 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5033 1.0656 1.2151 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1658 0.9261 1.9141 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8165 2.3343 2.4179 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0586 0.4747 1.0368 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4981 1.5802 0.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7762 1.2681 -0.5006 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7868 0.5380 0.3258 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2330 1.4334 1.4377 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4546 1.6067 -0.0265 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9885 0.7514 -0.9497 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1346 1.2826 -1.7526 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8043 0.1012 -2.4239 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8344 -0.8519 -3.0336 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5024 -0.9068 -2.3715 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4973 -1.4116 -3.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0445 0.2885 -1.8747 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7140 -0.6474 -4.4261 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7580 0.4925 -3.3550 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0399 1.9913 -1.0027 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7323 0.5895 3.5733 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9071 -0.4185 4.8552 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3614 -1.7482 0.3045 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3790 -0.6934 0.0761 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3737 -0.8359 -0.8713 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5223 -1.0197 -3.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0367 -2.7508 -2.7585 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6201 -2.3539 -3.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6080 -2.9590 -0.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8101 -2.6988 -3.1112 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4094 -3.2630 -1.4743 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0528 -1.3690 -2.2152 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5499 -0.3813 -2.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3529 0.5815 0.9940 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7468 2.1463 -1.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4302 1.4780 -1.6630 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0874 2.4061 -0.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6725 -0.0174 -1.5133 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 -2.2458 -0.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8702 -2.6244 1.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6727 -1.1411 2.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5812 -1.1480 -0.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5080 0.5050 2.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2467 -1.9546 2.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3168 -1.8720 3.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6286 -1.2282 4.5555 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6605 0.2696 4.1570 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0334 -0.8614 2.6196 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7876 1.2459 4.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7562 2.2438 4.1647 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0550 2.9630 2.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3957 1.9236 1.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9726 0.0396 1.1925 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4261 2.5969 3.3172 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7675 2.3714 2.7557 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0675 3.1076 1.6631 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4816 -0.2850 0.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2167 1.8824 -0.5986 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3288 2.5329 0.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2272 2.1815 -0.8851 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5598 0.6239 -1.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4240 2.1411 1.7287 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0184 2.1129 0.9896 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6602 0.8978 2.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3401 -0.1704 -0.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6971 1.8981 -2.5883 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3746 -0.4238 -1.6069 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2892 -1.8823 -2.9459 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4538 -1.6606 -1.5449 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6699 -0.8797 -4.3831 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4659 -1.2146 -3.0904 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6446 -2.4842 -3.6156 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4189 -1.1410 -4.9185 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3551 -0.2910 -3.4870 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8789 2.9572 -1.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0163 0.4921 4.5292 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1563 -1.1240 4.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4086 0.0376 -1.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3465 -0.8238 -0.3369 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 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 19 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 31 35 1 0 30 36 1 0 29 37 1 0 17 38 1 0 16 39 1 0 9 40 1 0 5 41 1 1 41 42 1 0 42 2 1 0 40 5 1 0 25 8 1 0 34 28 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 1 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 6 51 1 1 7 52 1 0 7 53 1 0 7 54 1 0 8 55 1 6 9 56 1 6 10 57 1 0 10 58 1 0 11 59 1 6 12 60 1 1 13 61 1 0 13 62 1 0 14 63 1 0 14 64 1 0 15 65 1 6 16 66 1 1 17 67 1 1 18 68 1 0 18 69 1 0 19 70 1 6 21 71 1 0 21 72 1 0 21 73 1 0 22 74 1 6 23 75 1 0 23 76 1 0 24 77 1 0 24 78 1 0 26 79 1 0 26 80 1 0 26 81 1 0 28 82 1 1 29 83 1 6 30 84 1 1 31 85 1 6 32 86 1 1 33 87 1 0 33 88 1 0 33 89 1 0 35 90 1 0 36 91 1 0 37 92 1 0 38 93 1 0 39 94 1 0 42 95 1 0 42 96 1 0 M END

Standard InCHIKey	CNASGYYQUHJFQY-NFZOLUOBSA-N
Standard InCHI	InChI=1S/C33H54O9/c1-15-8-11-33(39-14-15)16(2)25-23(42-33)12-21-18-6-7-20-27(36)22(34)13-24(32(20,5)19(18)9-10-31(21,25)4)41-30-29(38)28(37)26(35)17(3)40-30/h15-30,34-38H,6-14H2,1-5H3/t15-,16+,17-,18-,19+,20+,21+,22-,23+,24-,25+,26+,27+,28+,29-,30+,31+,32-,33+/m1/s1
SMILES	C[C@@H]1CC[C@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC[C@H]6[C@@H]([C@@H](C[C@H]([C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@H]([C@@H](C)O3)O)O)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.38	Volume:	598.541 ? Van der Waals volume.
Dense:	0.993	LogP:	4.398 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.246 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.982 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	36.0
TPSA:	138.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	7.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.327	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.029	Fsp³:	1.0
MCE-18:	177.03 ? 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:	0.747	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.039 ? 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:	0.202	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.757	MDCK Permeability:	-5.095
Pgp-inhibitor:	0.0	Pgp-substrate:	0.66
PAMPA:	0.998 ? 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):	0.237
20% Bioavailability (F20%):	0.938	30% Bioavailability (F30%):	0.947
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.728	MRP1:	0.542
Plasma Protein Binding (PPB):	71.955%	Volume Distribution (VD):	-0.269
Fu:	21.732% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.491
BSEP inhibitor:	0.02

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.885
HLM stability:	0.328 ? 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):

2.61

Half-life (T1/2):

2.181

ADMET: Toxicity

hERG Blockers:	0.115	hERG Blockers (10um):	0.526
Human Hepatotoxicity (H-HT):	0.493	Drug-induced Liver Injury (DILI):	0.674
AMES Toxicity:	0.877	Rat Oral Acute Toxicity:	0.489
Maximum Recommended Daily Dose:	0.44	Skin Sensitization:	1.0
Carcinogencity:	0.641	Eye Corrosion:	0.0
Eye Irritation:	0.04	Respiratory Toxicity:	0.459
Drug-induced Neurotoxicity:	0.087	Ototoxicity:	0.877
Hematotoxicity:	0.303	Drug-induced Nephrotoxicity:	0.714
Genotoxicity:	0.231	RPMI-8226 Immunitoxicity:	0.325
A549 Cytotoxicity:	0.984	Hek293 Cytotoxicity:	0.96
BCF:	2.311 ? 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:	3.777 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.646 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.394 ? 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
NPO40087	Cordyline manners-suttoniae	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31596585]
NPO40087	Cordyline manners-suttoniae	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	2
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
NPT941	Cell line	HaCaT	Homo sapiens	IC50	=	74900.0	nM	PMID[31596585]
NPT3190	Cell line	NHDF	Homo sapiens	IC50	=	6600.0	nM	PMID[31596585]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	3.0	n.a.	PMID[31596585]

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 NPC481421 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	26745
0.1-0.2	20986
0.2-0.3	1827
0.3-0.4	133
0.4-0.5	98
0.5-0.6	53
0.6-0.7	7
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC481420
0.8442	Intermediate Similarity	NPC481425
0.8442	Intermediate Similarity	NPC481426
0.7692	Intermediate Similarity	NPC473774
0.7692	Intermediate Similarity	NPC481419
0.7692	Intermediate Similarity	NPC481417
0.6747	Remote Similarity	NPC24960
0.6512	Remote Similarity	NPC481424
0.6512	Remote Similarity	NPC481422
0.6463	Remote Similarity	NPC144790
0.6463	Remote Similarity	NPC149400
0.6235	Remote Similarity	NPC481418
0.6023	Remote Similarity	NPC485594
0.5934	Remote Similarity	NPC477451
0.5914	Remote Similarity	NPC306131
0.5914	Remote Similarity	NPC200802
0.5895	Remote Similarity	NPC485595
0.587	Remote Similarity	NPC222731
0.5833	Remote Similarity	NPC70204
0.5824	Remote Similarity	NPC131693
0.5824	Remote Similarity	NPC475436
0.5745	Remote Similarity	NPC19400
0.5699	Remote Similarity	NPC473616
0.5632	Remote Similarity	NPC277715
0.5567	Remote Similarity	NPC6295
0.5543	Remote Similarity	NPC297348
0.5543	Remote Similarity	NPC325828
0.5543	Remote Similarity	NPC249204
0.5543	Remote Similarity	NPC48339
0.5543	Remote Similarity	NPC177834
0.5543	Remote Similarity	NPC141769
0.5543	Remote Similarity	NPC477547
0.551	Remote Similarity	NPC195297
0.5484	Remote Similarity	NPC294686
0.5484	Remote Similarity	NPC234352
0.5443	Remote Similarity	NPC296734
0.5408	Remote Similarity	NPC470432
0.5408	Remote Similarity	NPC230507
0.5385	Remote Similarity	NPC294129
0.5316	Remote Similarity	NPC248944
0.5316	Remote Similarity	NPC227260
0.5316	Remote Similarity	NPC7479
0.5316	Remote Similarity	NPC257296
0.5312	Remote Similarity	NPC206003
0.5312	Remote Similarity	NPC473610
0.53	Remote Similarity	NPC113044
0.53	Remote Similarity	NPC283829
0.53	Remote Similarity	NPC14704
0.53	Remote Similarity	NPC161676
0.5269	Remote Similarity	NPC181845
0.5269	Remote Similarity	NPC481423
0.5258	Remote Similarity	NPC211354
0.5258	Remote Similarity	NPC107188
0.525	Remote Similarity	NPC273290
0.525	Remote Similarity	NPC232044
0.5208	Remote Similarity	NPC250393
0.5169	Remote Similarity	NPC88962
0.5152	Remote Similarity	NPC107962
0.5146	Remote Similarity	NPC470433
0.5146	Remote Similarity	NPC46190
0.5146	Remote Similarity	NPC171073
0.5146	Remote Similarity	NPC602423
0.505	Remote Similarity	NPC141433
0.505	Remote Similarity	NPC475670
0.5048	Remote Similarity	NPC471464
0.5048	Remote Similarity	NPC300557

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC481421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7668
0.1-0.2	1426
0.2-0.3	48
0.3-0.4	4
0.4-0.5	2
0.5-0.6	2
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
0.5543	Remote Similarity	NPD8171	Phase 2
0.5316	Remote Similarity	NPD6928	Phase 2

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