NPASS Compound

Natural Product: NPC248294

Natural Product ID	NPC248294
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QJYNZEYHSMRWBK-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	374874
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 99104 0 0 0 0 0 0 0 0999 V2000 1.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0905 -5.7092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 -7.1864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9791 -8.1506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3886 -7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6491 -6.1603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8886 -7.6375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6386 -8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0525 -10.3174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1386 -8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8886 -10.2356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3886 -10.2356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1386 -8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3886 -7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8886 -7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1386 -6.3385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.6386 -8.9366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1386 -11.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7291 -9.4496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9791 -10.7487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4902 -10.9315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7291 -12.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9791 -13.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7291 -14.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -14.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9791 -13.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -12.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4791 -13.3467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9791 -15.9448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9791 -15.9448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0800 -8.4854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -8.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3228 -7.2875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6700 -9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -11.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6700 -12.3825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -12.3825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -11.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -13.6816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -13.6816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9200 -11.0835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 -5.7092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8405 -4.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 -3.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6595 -4.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4095 -5.7092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9095 -5.7092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -4.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9095 -3.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4095 -3.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -4.4101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -7.0082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0490 -3.1471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0162 -4.2086 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6491 -4.2320 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8574 -4.9469 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 -6.6734 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 -9.1148 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6491 -9.1148 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1386 -11.5347 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1386 -6.3385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3886 -5.0395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3886 -7.6375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6386 -11.5347 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4791 -13.3467 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1318 -10.8498 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2291 -14.6458 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4791 -15.9448 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7291 -17.2438 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -8.4854 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0688 -11.2664 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -14.9806 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6700 -14.9806 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6700 -12.3825 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8235 -7.0900 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6595 -1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9095 -3.1111 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -7.0082 0.0000 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 5 8 1 0 4 9 1 0 2 10 1 0 10 11 2 0 10 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 18 20 1 0 20 21 1 0 21 22 2 0 21 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 25 31 1 0 17 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 39 41 1 0 38 42 1 0 37 43 1 0 16 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 51 53 1 0 50 54 1 0 49 55 1 0 15 56 1 0 56 57 1 0 57 58 2 0 57 59 1 0 59 60 2 0 60 61 1 0 61 62 2 0 62 63 1 0 63 64 2 0 63 65 1 0 62 66 1 0 61 67 1 0 6 1 1 0 19 14 1 0 28 23 1 0 40 35 1 0 52 47 1 0 64 59 1 0 1 68 1 0 3 69 1 0 7 70 1 0 8 71 1 0 9 72 1 0 13 73 1 0 13 74 1 0 14 75 1 0 15 76 1 0 16 77 1 0 17 78 1 0 18 79 1 0 24 80 1 0 28 81 1 0 29 82 1 0 30 83 1 0 31 84 1 0 36 85 1 0 40 86 1 0 41 87 1 0 42 88 1 0 43 89 1 0 48 90 1 0 52 91 1 0 53 92 1 0 54 93 1 0 55 94 1 0 60 95 1 0 64 96 1 0 65 97 1 0 66 98 1 0 67 99 1 0 M END

Standard InCHIKey	QJYNZEYHSMRWBK-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2
SMILES	c1c(cc(c(c1O)O)O)C(=O)OCC1C(C(C(C(O1)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	940.12	Volume:	842.17 ? Van der Waals volume.
Dense:	1.116	LogP:	1.345 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.706 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.9 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	41.0
TPSA:	444.18 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	15.0	Rings:	6.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.051	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.753	Fsp³:	0.146
MCE-18:	154.213 ? 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:	0.994	Fluc inhibitor:	0.036 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.213 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.778	Promiscuous compounds:	0.939

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.682	MDCK Permeability:	-4.739
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
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):	0.0
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):	68.903%	Volume Distribution (VD):	-0.206
Fu:	16.413% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.783	BCRP inhibitor:	0.999
BSEP inhibitor:	0.007

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.454
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.928 ? 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):

6.261

Half-life (T1/2):

3.744

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.999
Human Hepatotoxicity (H-HT):	0.002	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.635	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.96	Skin Sensitization:	1.0
Carcinogencity:	0.023	Eye Corrosion:	0.0
Eye Irritation:	0.808	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.681
BCF:	0.368 ? 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:	3.594 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.502 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.458 ? 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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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 NPC248294 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	24687
0.1-0.2	24199
0.2-0.3	792
0.3-0.4	78
0.4-0.5	53
0.5-0.6	31
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC114791
1.0	High Similarity	NPC104222
1.0	High Similarity	NPC210501
1.0	High Similarity	NPC318826
1.0	High Similarity	NPC141331
0.7963	Intermediate Similarity	NPC43918
0.7963	Intermediate Similarity	NPC261411
0.7963	Intermediate Similarity	NPC190204
0.7818	Intermediate Similarity	NPC469651
0.7778	Intermediate Similarity	NPC47521
0.7414	Intermediate Similarity	NPC149300
0.64	Remote Similarity	NPC610546
0.625	Remote Similarity	NPC238419
0.625	Remote Similarity	NPC172419
0.6056	Remote Similarity	NPC112211
0.6056	Remote Similarity	NPC254925
0.6027	Remote Similarity	NPC290289
0.5965	Remote Similarity	NPC283806
0.589	Remote Similarity	NPC223534
0.589	Remote Similarity	NPC483712
0.589	Remote Similarity	NPC158214
0.589	Remote Similarity	NPC214202
0.5818	Remote Similarity	NPC239019
0.5818	Remote Similarity	NPC247629
0.5714	Remote Similarity	NPC44260
0.5676	Remote Similarity	NPC97924
0.5584	Remote Similarity	NPC187632
0.5584	Remote Similarity	NPC240200
0.5584	Remote Similarity	NPC488885
0.5517	Remote Similarity	NPC205037
0.5517	Remote Similarity	NPC3746
0.5479	Remote Similarity	NPC40078
0.5443	Remote Similarity	NPC194439
0.5443	Remote Similarity	NPC33724
0.5439	Remote Similarity	NPC124639
0.5362	Remote Similarity	NPC8940
0.5309	Remote Similarity	NPC116108
0.5181	Remote Similarity	NPC7839
0.5181	Remote Similarity	NPC488884
0.5181	Remote Similarity	NPC142291
0.5172	Remote Similarity	NPC92117
0.5152	Remote Similarity	NPC302170
0.5152	Remote Similarity	NPC311389
0.5119	Remote Similarity	NPC488887
0.5119	Remote Similarity	NPC488886
0.5085	Remote Similarity	NPC61152
0.5085	Remote Similarity	NPC125546
0.5062	Remote Similarity	NPC189312

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC248294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5824
0.1-0.2	3296
0.2-0.3	28
0.3-0.4	1
0.4-0.5	1
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