NPASS Compound

Natural Product: NPC106944

Natural Product ID	NPC106944
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Plantagineoside B
IUPAC Name	(2S,3R,4S,5S,6R)-2-[2-hydroxy-4-[(5S)-5-hydroxy-7-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]heptyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms	plantagineoside B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2159606
PubChem CID	71449654
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

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 90 93 0 0 0 0 0 0 0 0999 V2000 7.1221 1.4340 -4.6681 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4931 2.2193 -3.5862 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1440 1.3445 -2.5519 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2192 0.3698 -2.1559 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7019 -0.2376 -0.9609 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7195 -1.1567 -0.6012 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7986 -0.9622 0.4091 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7326 0.1663 1.1947 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7791 0.3017 2.1913 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8573 -0.6792 2.4433 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9034 -1.8155 1.6742 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8458 -1.9548 0.6857 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8945 -3.1000 -0.0914 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8426 -0.4503 3.5201 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6509 0.2358 2.9266 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5517 0.5286 3.8813 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0610 -0.6471 4.5197 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6463 -1.7342 3.7482 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7528 -1.4782 2.8257 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5727 -0.5901 1.6590 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8717 -0.5955 0.8963 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1560 -1.5239 -0.0795 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3281 -1.5052 -0.7794 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3281 -0.5284 -0.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0125 0.3827 0.4339 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8077 0.3537 1.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9302 1.3902 0.7462 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4572 -0.5961 -1.2957 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5414 0.2196 -1.3229 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7195 -0.4086 -0.8560 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5872 0.5648 -0.4454 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.9650 -0.0453 -0.2075 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8591 0.9383 0.2098 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6427 1.7885 -1.2828 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0351 1.6322 -2.6494 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9208 0.6550 -2.7463 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8201 1.1206 -3.4316 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0318 1.3948 -3.6241 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0707 2.9086 -0.6355 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3357 -2.4707 3.0242 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9939 -0.9850 -1.2858 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9927 -0.1235 -1.9843 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3221 0.5935 -3.1297 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2079 1.4850 -3.7595 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9421 -0.9910 -2.5719 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4629 -1.5525 -0.1151 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7712 1.9835 -5.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5999 2.7113 -3.1303 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2532 2.9783 -3.8907 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4654 1.9575 -1.6595 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8471 0.6010 -0.2807 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4412 0.9811 1.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7789 1.2146 2.7754 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1744 -2.6146 1.8612 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7579 -3.6617 -0.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3322 0.2090 4.2777 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6351 -1.4127 4.0059 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0262 1.2228 2.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2821 -0.3621 2.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0806 1.1218 4.7480 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1910 1.2091 3.4636 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8159 -0.2256 5.2846 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7270 -1.0564 5.2640 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0782 -2.4735 4.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1933 -2.4489 2.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6198 -1.0944 3.4476 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3843 0.4621 1.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8072 -1.0065 0.9603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4153 -2.2986 -0.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5551 -2.2455 -1.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6444 1.1008 1.8908 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1474 1.6251 1.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4862 1.1606 -0.7551 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2472 0.8789 0.5865 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9390 -0.8016 0.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3389 -0.4894 -1.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3615 1.7124 0.5724 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7115 2.0577 -1.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6273 2.6429 -2.9389 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2891 -0.2854 -3.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4305 0.4951 -4.0715 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7331 0.6915 -4.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0574 2.7766 0.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2027 -3.1335 2.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6955 -1.7987 -1.9992 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4868 0.5830 -1.2824 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9373 -0.1619 -3.8369 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8223 1.8673 -4.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4497 -0.5263 -3.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3162 -2.0428 -0.3350 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 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 10 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 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 24 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 35 38 1 0 34 39 1 0 18 40 1 0 5 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 43 3 1 0 12 7 1 0 26 21 1 0 36 29 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 1 5 51 1 1 8 52 1 0 9 53 1 0 11 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 17 63 1 0 18 64 1 1 19 65 1 0 19 66 1 0 20 67 1 0 20 68 1 0 22 69 1 0 23 70 1 0 26 71 1 0 27 72 1 0 29 73 1 1 31 74 1 1 32 75 1 0 32 76 1 0 33 77 1 0 34 78 1 6 35 79 1 6 36 80 1 6 37 81 1 0 38 82 1 0 39 83 1 0 40 84 1 0 41 85 1 6 42 86 1 1 43 87 1 6 44 88 1 0 45 89 1 0 46 90 1 0 M END

Standard InCHIKey	GPTLRCCVBQZPIL-BTNSERKDSA-N
Standard InCHI	InChI=1S/C31H44O15/c32-13-22-24(37)26(39)28(41)30(45-22)43-20-9-6-15(11-18(20)35)3-1-2-4-17(34)8-5-16-7-10-21(19(36)12-16)44-31-29(42)27(40)25(38)23(14-33)46-31/h6-7,9-12,17,22-42H,1-5,8,13-14H2/t17-,22+,23+,24+,25+,26-,27-,28+,29+,30+,31+/m0/s1
SMILES	OC[C@H]1O[C@@H](Oc2ccc(cc2O)CCCC[C@@H](CCc2ccc(c(c2)O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	656.27	Volume:	626.541 ? Van der Waals volume.
Dense:	1.047	LogP:	0.538 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.171 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.188 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	24.0
TPSA:	259.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	11.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.1	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.739	Fsp³:	0.613
MCE-18:	98.6 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.553	Fluc inhibitor:	0.298 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.299 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.153	Promiscuous compounds:	0.138

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.476	MDCK Permeability:	-5.146
Pgp-inhibitor:	0.0	Pgp-substrate:	0.334
PAMPA:	0.975 ? 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):	0.996
20% Bioavailability (F20%):	0.933	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.001
Plasma Protein Binding (PPB):	74.65%	Volume Distribution (VD):	-0.294
Fu:	17.748% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.177
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.016	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.011	CYP3A4-substrate:	0.201
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.311 ? 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):

1.312

Half-life (T1/2):

3.565

ADMET: Toxicity

hERG Blockers:	0.074	hERG Blockers (10um):	0.197
Human Hepatotoxicity (H-HT):	0.845	Drug-induced Liver Injury (DILI):	0.598
AMES Toxicity:	0.818	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	1.0
Carcinogencity:	0.003	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.247	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.335
A549 Cytotoxicity:	0.951	Hek293 Cytotoxicity:	0.369
BCF:	0.861 ? 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:	3.702 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.354 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.454 ? 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
NPO26380	Tacca plantaginea	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23031596]
NPO26380	Tacca plantaginea	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26380	Tacca plantaginea	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26380	Tacca plantaginea	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26380	Tacca plantaginea	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26380	Tacca plantaginea	Species	Taccaceae	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
FC	2
EC50	4
IC50	1

Activity Type	# Activity
Individual protein	5
Protein family	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	EC50	=	13100.0	nM	PMID[97381]
NPT866	Individual protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	EC50	>	50000.0	nM	PMID[22180047]
NPT866	Individual protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	FC	=	1.3	n.a.	PMID[20696876]
NPT99	Individual protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	FC	=	1.5	n.a.	PMID[25338180]
NPT99	Individual protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	33100.0	nM	PMID[23701598]
NPT3942	Protein family	Peroxisome proliferator-activated receptor	Homo sapiens	EC50	=	10400.0	nM	PMID[16872131]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	>	10000.0	nM	PMID[16872131]

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 NPC106944 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	13986
0.1-0.2	30750
0.2-0.3	4144
0.3-0.4	724
0.4-0.5	228
0.5-0.6	19
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
0.7538	Intermediate Similarity	NPC116229
0.6885	Remote Similarity	NPC19470
0.6389	Remote Similarity	NPC476411
0.6	Remote Similarity	NPC9248
0.5758	Remote Similarity	NPC481303
0.5735	Remote Similarity	NPC59324
0.5556	Remote Similarity	NPC189115
0.5522	Remote Similarity	NPC210015
0.5429	Remote Similarity	NPC100389
0.5397	Remote Similarity	NPC60589
0.5397	Remote Similarity	NPC469708
0.5278	Remote Similarity	NPC186418
0.5278	Remote Similarity	NPC202700
0.5152	Remote Similarity	NPC166168
0.5147	Remote Similarity	NPC205054
0.5139	Remote Similarity	NPC469661
0.5135	Remote Similarity	NPC98777
0.5075	Remote Similarity	NPC9912
0.5072	Remote Similarity	NPC26653
0.5072	Remote Similarity	NPC80600
0.5068	Remote Similarity	NPC479374
0.5065	Remote Similarity	NPC191046
0.5063	Remote Similarity	NPC232228

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC106944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3148
0.1-0.2	5812
0.2-0.3	179
0.3-0.4	8
0.4-0.5	3
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