NPASS Compound

Natural Product: NPC182280

Natural Product ID	NPC182280
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LQQNPVZIFKLQPE-USGPILJJSA-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:0001586] Biflavonoids and polyflavonoids

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 84 90 0 0 0 0 0 0 0 0999 V2000 0.1058 -3.0629 1.3983 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2993 -4.3427 1.6699 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2520 -5.3578 0.9106 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1742 -5.0599 -0.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5829 -3.7655 -0.3510 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0220 -2.7377 0.4210 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4130 -1.3243 0.1873 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3956 -0.8851 1.2198 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7724 0.0400 2.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0331 1.1267 1.5999 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1063 2.4246 2.0070 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3876 3.3922 1.3334 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4091 3.1128 0.2591 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4941 1.7828 -0.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3357 1.4054 -1.3001 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6709 -0.0461 -1.1571 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2251 -1.0467 -1.9475 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6486 -2.3501 -1.7173 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5256 -2.6423 -0.6841 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9817 -1.6095 0.1269 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5473 -0.3292 -0.1234 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9870 0.7490 0.6715 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3936 1.9764 0.0318 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8706 1.8710 -0.0884 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5575 1.4113 1.0330 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9316 1.2741 1.0342 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6224 1.6045 -0.1099 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9689 2.0663 -1.2468 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5921 2.1848 -1.1938 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6691 2.3995 -2.4017 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0077 1.4811 -0.1514 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6338 0.8147 2.1503 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7201 2.0390 -1.2939 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8335 3.2074 -1.9944 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9460 -3.9459 -0.4577 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3495 -0.7874 -2.9861 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2228 0.8030 0.4987 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2302 -0.5426 0.1823 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1184 4.0824 -0.4073 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9055 2.7455 3.0946 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4910 -0.1635 0.6480 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8144 -0.5332 0.8283 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0447 -1.5472 1.5259 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9175 0.2343 0.2239 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2079 -0.1825 0.4433 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2667 0.5158 -0.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0633 1.6241 -0.8801 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7530 2.0281 -1.0894 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6875 1.3417 -0.5438 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5556 3.1566 -1.8740 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1088 2.3428 -1.4473 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5936 0.1065 0.1018 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7150 -6.0979 -0.8282 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1624 -6.6514 1.1906 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3173 -2.2606 1.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0243 -4.5090 2.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3023 -3.5210 -1.1201 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9153 -1.2218 -0.8142 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7881 -1.7499 1.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0811 -0.5447 2.8711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6384 0.4364 2.8514 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4595 4.4261 1.6743 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8901 1.5875 -2.2773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3137 -3.1713 -2.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6685 -1.8527 0.9338 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1888 2.7660 0.7424 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0311 1.1498 1.9328 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0727 2.5411 -2.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8745 1.7204 -3.1146 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5339 2.0484 -0.7827 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9241 1.3987 2.9053 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3384 1.3182 -1.9395 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6661 3.0294 -2.9525 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7068 -4.1232 0.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3065 -1.2973 -3.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6505 4.7405 -1.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8574 2.1736 3.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4369 -1.0675 1.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6773 1.6704 -0.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9284 3.2670 -2.7981 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1960 3.3545 -1.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2371 0.7322 0.6023 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6539 -6.3989 -0.5913 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9855 -6.9755 0.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 26 32 1 0 23 33 1 0 33 34 1 0 19 35 1 0 17 36 1 0 14 37 2 0 37 38 1 0 13 39 1 0 11 40 1 0 8 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 48 50 1 0 47 51 1 0 46 52 1 0 4 53 1 0 3 54 1 0 6 1 1 0 38 7 1 0 49 44 1 0 37 10 1 0 33 15 1 0 21 16 1 0 29 24 1 0 1 55 1 0 2 56 1 0 5 57 1 0 7 58 1 6 8 59 1 1 9 60 1 0 9 61 1 0 12 62 1 0 15 63 1 6 18 64 1 0 20 65 1 0 23 66 1 1 25 67 1 0 29 68 1 0 30 69 1 0 31 70 1 0 32 71 1 0 33 72 1 6 34 73 1 0 35 74 1 0 36 75 1 0 39 76 1 0 40 77 1 0 45 78 1 0 49 79 1 0 50 80 1 0 51 81 1 0 52 82 1 0 53 83 1 0 54 84 1 0 M END

Standard InCHIKey	LQQNPVZIFKLQPE-USGPILJJSA-N
Standard InCHI	InChI=1S/C37H30O17/c38-15-8-20(42)28-26(9-15)52-35(13-4-22(44)31(48)23(45)5-13)33(50)30(28)29-21(43)11-18(40)16-10-27(53-37(51)14-6-24(46)32(49)25(47)7-14)34(54-36(16)29)12-1-2-17(39)19(41)3-12/h1-9,11,27,30,33-35,38-50H,10H2/t27-,30+,33-,34+,35+/m0/s1
SMILES	c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc(c([C@H]3c4c(cc(cc4O[C@H](c4cc(c(c(c4)O)O)O)[C@H]3O)O)O)c2O1)O)O)OC(=O)c1cc(c(c(c1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	746.15	Volume:	695.863 ? Van der Waals volume.
Dense:	1.072	LogP:	1.433 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.348 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.134 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	41.0
TPSA:	307.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.09	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.926	Fsp³:	0.162
MCE-18:	154.116 ? 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:	1
Colloidal aggregators:	0.977	Fluc inhibitor:	0.161 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.327 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.635 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.59	Promiscuous compounds:	0.635

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.612	MDCK Permeability:	-4.771
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
PAMPA:	0.54 ? 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):	0.0
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	90.115%	Volume Distribution (VD):	-0.061
Fu:	12.572% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.589
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

4.449

Half-life (T1/2):

4.837

ADMET: Toxicity

hERG Blockers:	0.051	hERG Blockers (10um):	0.985
Human Hepatotoxicity (H-HT):	0.472	Drug-induced Liver Injury (DILI):	0.971
AMES Toxicity:	0.591	Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.987	Skin Sensitization:	1.0
Carcinogencity:	0.02	Eye Corrosion:	0.0
Eye Irritation:	0.959	Respiratory Toxicity:	0.397
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.002
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.001
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.958
BCF:	0.961 ? 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:	3.703 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.958 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.344 ? 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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 16712885]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37255739]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8258	Camellia sinensis	Species	Theaceae	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 NPC182280 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	18713
0.1-0.2	28124
0.2-0.3	2732
0.3-0.4	156
0.4-0.5	67
0.5-0.6	33
0.6-0.7	25
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
0.8986	High Similarity	NPC65333
0.7733	Intermediate Similarity	NPC98583
0.7143	Intermediate Similarity	NPC38779
0.7143	Intermediate Similarity	NPC114179
0.7143	Intermediate Similarity	NPC68324
0.7143	Intermediate Similarity	NPC289322
0.7143	Intermediate Similarity	NPC160512
0.6842	Remote Similarity	NPC100251
0.6667	Remote Similarity	NPC135021
0.6622	Remote Similarity	NPC58190
0.6622	Remote Similarity	NPC108811
0.6622	Remote Similarity	NPC170103
0.6622	Remote Similarity	NPC236202
0.6622	Remote Similarity	NPC262911
0.6622	Remote Similarity	NPC202742
0.6575	Remote Similarity	NPC96576
0.6533	Remote Similarity	NPC246202
0.6533	Remote Similarity	NPC224161
0.6533	Remote Similarity	NPC46335
0.6533	Remote Similarity	NPC279406
0.6533	Remote Similarity	NPC486519
0.6438	Remote Similarity	NPC156818
0.6197	Remote Similarity	NPC291948
0.6197	Remote Similarity	NPC104983
0.6197	Remote Similarity	NPC250436
0.6197	Remote Similarity	NPC300845
0.6197	Remote Similarity	NPC88803
0.6173	Remote Similarity	NPC278548
0.6049	Remote Similarity	NPC600630
0.6049	Remote Similarity	NPC607896
0.6049	Remote Similarity	NPC611369
0.6	Remote Similarity	NPC474656
0.5974	Remote Similarity	NPC601196
0.5753	Remote Similarity	NPC178054
0.575	Remote Similarity	NPC53889
0.5732	Remote Similarity	NPC226809
0.5732	Remote Similarity	NPC601997
0.5732	Remote Similarity	NPC609211
0.5732	Remote Similarity	NPC610665
0.5556	Remote Similarity	NPC313116
0.5556	Remote Similarity	NPC86630
0.5556	Remote Similarity	NPC603340
0.5542	Remote Similarity	NPC211561
0.5506	Remote Similarity	NPC147743
0.5506	Remote Similarity	NPC4809
0.5506	Remote Similarity	NPC73517
0.55	Remote Similarity	NPC294558
0.55	Remote Similarity	NPC18185
0.55	Remote Similarity	NPC263940
0.5495	Remote Similarity	NPC106601
0.5495	Remote Similarity	NPC151474
0.5435	Remote Similarity	NPC212614
0.5435	Remote Similarity	NPC205613
0.5432	Remote Similarity	NPC603842
0.5422	Remote Similarity	NPC70409
0.5422	Remote Similarity	NPC204770
0.5422	Remote Similarity	NPC600551
0.5422	Remote Similarity	NPC601980
0.5422	Remote Similarity	NPC602065
0.5422	Remote Similarity	NPC611024
0.5312	Remote Similarity	NPC484330
0.5309	Remote Similarity	NPC87317
0.5301	Remote Similarity	NPC603291
0.5263	Remote Similarity	NPC159526
0.5161	Remote Similarity	NPC600812

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC182280 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5040
0.1-0.2	4081
0.2-0.3	21
0.3-0.4	4
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
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
0.6197	Remote Similarity	NPD4868	Phase 3

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