NPASS Compound

Natural Product: NPC76606

Natural Product ID	NPC76606
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GTKBXDKMEHYUSU-HQACPATNSA-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:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-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 93 98 0 0 0 0 0 0 0 0999 V2000 -11.0188 1.6078 -1.1135 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1939 0.4869 -0.5162 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.0730 -0.6343 -1.5339 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4502 -1.8246 -0.8125 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5250 -1.3459 0.2804 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9447 0.0331 -0.0615 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1246 -0.0002 -1.1104 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8364 0.2827 -1.1535 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3147 1.6623 -0.8809 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6026 2.1746 0.5015 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4060 3.1292 0.8029 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2743 2.1906 1.0904 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0823 1.3128 -0.1519 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1368 -0.0281 0.1419 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0992 -0.8915 0.3207 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3721 -2.2495 0.5853 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3346 -3.1244 0.7679 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0249 -2.6745 0.6922 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0478 -3.5267 0.8712 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8213 -4.7332 1.1057 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3301 -2.9950 0.7801 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5596 -1.6629 0.5204 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9177 -1.0956 0.4240 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9863 0.2653 0.1521 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2221 0.8230 0.0635 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4135 0.1022 0.2312 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3188 -1.2321 0.4970 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0549 -1.8291 0.5928 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4203 -2.0258 0.6778 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5663 0.7982 0.1144 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8855 0.4416 0.2150 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5697 1.3159 1.2916 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0479 1.2494 1.1351 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5449 0.2294 0.1649 C 0 0 2 0 0 0 0 0 0 0 0 0 10.7476 0.1606 -1.0997 C 0 0 2 0 0 0 0 0 0 0 0 0 11.5020 0.8202 -2.2458 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7414 0.2252 -2.4479 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5243 0.8354 -0.9863 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6892 -1.0417 0.7539 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6038 2.5172 0.8424 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0986 1.0208 2.5593 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4993 -0.9145 0.3619 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2648 -1.3565 0.4360 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8102 -0.4718 0.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6143 -4.4442 1.0250 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9682 1.6690 -1.1080 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1113 2.8392 1.4725 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7147 3.9557 1.8633 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7765 2.9138 0.5933 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9485 0.9793 -0.2546 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1621 -1.3497 1.5116 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8502 -2.7111 -1.6995 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2842 -0.9387 -2.1293 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0357 1.2363 -1.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9756 2.4962 -0.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5781 1.9272 -2.0935 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7324 0.0727 0.3588 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3293 -0.3007 -2.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2863 -2.3643 -0.3225 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6659 -2.0385 0.3198 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4293 0.3325 0.8683 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2324 -0.4581 -0.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4653 -0.0325 -2.2034 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8484 2.3480 -1.6177 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4797 1.3785 1.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2203 3.6609 -0.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5759 1.4827 1.9121 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0097 1.5737 -0.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4216 -2.5504 0.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1735 -3.6791 0.9232 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0784 0.8427 0.0181 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2926 1.8822 -0.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0092 -2.8849 0.8034 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3849 -3.0167 0.7734 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0932 -0.6210 0.4196 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1872 2.3506 1.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5069 0.9877 2.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5974 0.5319 -0.1112 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5662 -0.8967 -1.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6443 1.9134 -2.0484 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8928 0.7677 -3.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7831 -0.6783 -2.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3310 -1.7468 0.1913 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3607 2.4514 0.2102 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6238 1.7925 2.9907 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4865 0.5630 0.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6597 -5.1793 0.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 2.8868 0.7945 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4400 4.8713 1.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0637 2.8296 1.5584 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5282 -0.8966 2.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1381 -3.2272 -1.2474 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8265 -1.5479 -1.5555 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 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 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 26 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 35 38 1 0 34 39 1 0 33 40 1 0 32 41 1 0 22 42 1 0 42 43 1 0 43 44 2 0 17 45 1 0 13 46 1 0 12 47 1 0 11 48 1 0 10 49 1 0 6 50 1 0 5 51 1 0 4 52 1 0 3 53 1 0 50 2 1 0 46 9 1 0 44 15 1 0 43 18 1 0 28 23 1 0 38 31 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 1 3 58 1 6 4 59 1 1 5 60 1 1 6 61 1 1 8 62 1 0 8 63 1 0 9 64 1 6 10 65 1 1 11 66 1 6 12 67 1 1 13 68 1 6 16 69 1 0 21 70 1 0 24 71 1 0 25 72 1 0 28 73 1 0 29 74 1 0 31 75 1 1 32 76 1 6 33 77 1 1 34 78 1 6 35 79 1 6 36 80 1 0 36 81 1 0 37 82 1 0 39 83 1 0 40 84 1 0 41 85 1 0 44 86 1 0 45 87 1 0 47 88 1 0 48 89 1 0 49 90 1 0 51 91 1 0 52 92 1 0 53 93 1 0 M END

Standard InCHIKey	GTKBXDKMEHYUSU-HQACPATNSA-N
Standard InCHI	InChI=1S/C33H40O20/c1-10-22(38)25(41)28(44)31(48-10)47-9-20-24(40)27(43)29(45)32(53-20)49-12-5-14(36)21-15(37)7-17(50-18(21)6-12)11-2-3-16(13(35)4-11)51-33-30(46)26(42)23(39)19(8-34)52-33/h2-7,10,19-20,22-36,38-46H,8-9H2,1H3/t10-,19-,20-,22-,23-,24-,25+,26+,27+,28-,29-,30-,31-,32-,33-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](OC[C@H]2[C@@H]([C@H]([C@@H]([C@@H](Oc3cc(c4c(=O)cc(c5ccc(c(c5)O)O[C@@H]5[C@H]([C@@H]([C@H]([C@H](CO)O5)O)O)O)oc4c3)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.21	Volume:	682.698 ? Van der Waals volume.
Dense:	1.108	LogP:	0.209 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.15 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.211 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	328.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.099	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.338	Fsp³:	0.545
MCE-18:	150.706 ? 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:	0.678	Fluc inhibitor:	0.36 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.891 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.565 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.208	Promiscuous compounds:	0.468

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.899	MDCK Permeability:	-4.879
Pgp-inhibitor:	0.0	Pgp-substrate:	0.821
PAMPA:	1.0 ? 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):	0.999
20% Bioavailability (F20%):	0.373	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.027
Plasma Protein Binding (PPB):	73.181%	Volume Distribution (VD):	-0.196
Fu:	24.363% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.168
BSEP inhibitor:	0.0

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.085
HLM stability:	0.0 ? 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):

0.793

Half-life (T1/2):

6.023

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.034
Human Hepatotoxicity (H-HT):	0.394	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.975	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	0.997
Carcinogencity:	0.007	Eye Corrosion:	0.0
Eye Irritation:	0.008	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.995
Hematotoxicity:	0.063	Drug-induced Nephrotoxicity:	0.891
Genotoxicity:	0.474	RPMI-8226 Immunitoxicity:	0.397
A549 Cytotoxicity:	0.507	Hek293 Cytotoxicity:	0.234
BCF:	0.367 ? 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:	2.734 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.45 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.496 ? 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
NPO18273	Merendera sobolifera	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5721	Psorothamnus spinosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18861	Pyxine coccifera	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18273	Merendera sobolifera	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16819	Preussia aemulans	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	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

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

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 NPC76606 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	20220
0.1-0.2	24973
0.2-0.3	3546
0.3-0.4	691
0.4-0.5	259
0.5-0.6	109
0.6-0.7	45
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC209296
0.7889	Intermediate Similarity	NPC22062
0.7889	Intermediate Similarity	NPC473634
0.7889	Intermediate Similarity	NPC210073
0.7889	Intermediate Similarity	NPC138811
0.7723	Intermediate Similarity	NPC198199
0.7582	Intermediate Similarity	NPC44931
0.75	Intermediate Similarity	NPC120952
0.75	Intermediate Similarity	NPC22832
0.699	Remote Similarity	NPC311850
0.6809	Remote Similarity	NPC251417
0.6792	Remote Similarity	NPC68592
0.6729	Remote Similarity	NPC298666
0.6667	Remote Similarity	NPC95090
0.6667	Remote Similarity	NPC27408
0.6667	Remote Similarity	NPC473623
0.6667	Remote Similarity	NPC189142
0.6667	Remote Similarity	NPC77660
0.663	Remote Similarity	NPC285197
0.6602	Remote Similarity	NPC11468
0.66	Remote Similarity	NPC488089
0.6571	Remote Similarity	NPC480441
0.6571	Remote Similarity	NPC25523
0.6566	Remote Similarity	NPC65711
0.6559	Remote Similarity	NPC601144
0.6531	Remote Similarity	NPC204693
0.6495	Remote Similarity	NPC67105
0.6471	Remote Similarity	NPC101636
0.6452	Remote Similarity	NPC191306
0.6429	Remote Similarity	NPC262222
0.6383	Remote Similarity	NPC243930
0.6383	Remote Similarity	NPC486578
0.6383	Remote Similarity	NPC605067
0.6374	Remote Similarity	NPC261866
0.6374	Remote Similarity	NPC39360
0.6374	Remote Similarity	NPC19709
0.6374	Remote Similarity	NPC29763
0.6374	Remote Similarity	NPC210003
0.6373	Remote Similarity	NPC475382
0.6364	Remote Similarity	NPC115674
0.6364	Remote Similarity	NPC186816
0.6327	Remote Similarity	NPC275454
0.6327	Remote Similarity	NPC227508
0.6316	Remote Similarity	NPC311830
0.6316	Remote Similarity	NPC607707
0.6296	Remote Similarity	NPC488083
0.6262	Remote Similarity	NPC473644
0.61	Remote Similarity	NPC65003
0.6095	Remote Similarity	NPC135358
0.6087	Remote Similarity	NPC473043
0.6087	Remote Similarity	NPC331652
0.6058	Remote Similarity	NPC195257
0.6019	Remote Similarity	NPC229409
0.6	Remote Similarity	NPC298171
0.598	Remote Similarity	NPC46202
0.596	Remote Similarity	NPC8856
0.5918	Remote Similarity	NPC190003
0.5865	Remote Similarity	NPC473327
0.5825	Remote Similarity	NPC475366
0.5825	Remote Similarity	NPC64051
0.581	Remote Similarity	NPC270675
0.581	Remote Similarity	NPC195685
0.5784	Remote Similarity	NPC479405
0.5784	Remote Similarity	NPC303913
0.5773	Remote Similarity	NPC611303
0.5752	Remote Similarity	NPC488086
0.5741	Remote Similarity	NPC14187
0.5729	Remote Similarity	NPC181712
0.5728	Remote Similarity	NPC479404
0.5714	Remote Similarity	NPC488087
0.5684	Remote Similarity	NPC289667
0.5657	Remote Similarity	NPC116458
0.5657	Remote Similarity	NPC246943
0.5657	Remote Similarity	NPC605784
0.5648	Remote Similarity	NPC472994
0.5619	Remote Similarity	NPC479403
0.5607	Remote Similarity	NPC256760
0.5588	Remote Similarity	NPC187379
0.5586	Remote Similarity	NPC472993
0.5567	Remote Similarity	NPC58716
0.5566	Remote Similarity	NPC483707
0.5521	Remote Similarity	NPC58053
0.5521	Remote Similarity	NPC143851
0.5514	Remote Similarity	NPC142142
0.551	Remote Similarity	NPC27942
0.5464	Remote Similarity	NPC277205
0.5464	Remote Similarity	NPC37919
0.5421	Remote Similarity	NPC32641
0.5421	Remote Similarity	NPC256188
0.5421	Remote Similarity	NPC35119
0.5408	Remote Similarity	NPC186807
0.54	Remote Similarity	NPC80188
0.5392	Remote Similarity	NPC211594
0.5378	Remote Similarity	NPC192539
0.5361	Remote Similarity	NPC45618
0.5354	Remote Similarity	NPC21100
0.5351	Remote Similarity	NPC277532
0.5347	Remote Similarity	NPC220169
0.534	Remote Similarity	NPC254540
0.5327	Remote Similarity	NPC470443
0.5306	Remote Similarity	NPC297987
0.5306	Remote Similarity	NPC168822
0.5306	Remote Similarity	NPC146792
0.5306	Remote Similarity	NPC136042
0.5306	Remote Similarity	NPC323593
0.5306	Remote Similarity	NPC203500
0.5294	Remote Similarity	NPC601586
0.5278	Remote Similarity	NPC606657
0.5273	Remote Similarity	NPC287889
0.5253	Remote Similarity	NPC84362
0.5253	Remote Similarity	NPC45638
0.5248	Remote Similarity	NPC601710
0.5238	Remote Similarity	NPC173582
0.5238	Remote Similarity	NPC265885
0.5238	Remote Similarity	NPC181465
0.5238	Remote Similarity	NPC215710
0.5238	Remote Similarity	NPC473438
0.5238	Remote Similarity	NPC253788
0.5234	Remote Similarity	NPC64425
0.5227	Remote Similarity	NPC223579
0.5204	Remote Similarity	NPC238376
0.52	Remote Similarity	NPC201292
0.5189	Remote Similarity	NPC203259
0.5189	Remote Similarity	NPC33054
0.5189	Remote Similarity	NPC176740
0.5189	Remote Similarity	NPC471725
0.5189	Remote Similarity	NPC134532
0.5189	Remote Similarity	NPC156869
0.5189	Remote Similarity	NPC602582
0.5182	Remote Similarity	NPC476472
0.5182	Remote Similarity	NPC294815
0.5182	Remote Similarity	NPC16194
0.5179	Remote Similarity	NPC244875
0.5149	Remote Similarity	NPC60735
0.5149	Remote Similarity	NPC26230
0.5149	Remote Similarity	NPC609451
0.5143	Remote Similarity	NPC295613
0.5143	Remote Similarity	NPC473657
0.5128	Remote Similarity	NPC488088
0.5126	Remote Similarity	NPC470719
0.5098	Remote Similarity	NPC284960
0.5098	Remote Similarity	NPC181616
0.5098	Remote Similarity	NPC609478
0.5096	Remote Similarity	NPC172807
0.5094	Remote Similarity	NPC39834
0.5093	Remote Similarity	NPC488073
0.5093	Remote Similarity	NPC126784
0.5093	Remote Similarity	NPC240306
0.5093	Remote Similarity	NPC241423
0.5089	Remote Similarity	NPC253685
0.5089	Remote Similarity	NPC602448
0.5053	Remote Similarity	NPC134819
0.5051	Remote Similarity	NPC249281
0.5051	Remote Similarity	NPC108831
0.5051	Remote Similarity	NPC182634
0.5049	Remote Similarity	NPC88023
0.5049	Remote Similarity	NPC309025
0.5049	Remote Similarity	NPC602805
0.5047	Remote Similarity	NPC473512
0.5047	Remote Similarity	NPC129827
0.5047	Remote Similarity	NPC102028
0.5047	Remote Similarity	NPC3583
0.5045	Remote Similarity	NPC473073

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC76606 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5230
0.1-0.2	3834
0.2-0.3	73
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD7054	Phase 4
0.6765	Remote Similarity	NPD7472	Pre-clinical
0.6132	Remote Similarity	NPD7808	Phase 3
0.6058	Remote Similarity	NPD7251	Phase 2
0.5189	Remote Similarity	NPD6797	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