NPASS Compound

Natural Product: NPC470827

Natural Product ID	NPC470827
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4''-O-(8-Guaiacylglycerol)Buddlenol A
IUPAC Name	(E)-3-[(2R,3S)-2-[4-[1-[4-[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]-1,3-dihydroxypropan-2-yl]oxy-3,5-dimethoxyphenyl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL225531
PubChem CID	16216400
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

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 102106 0 0 0 0 0 0 0 0999 V2000 14.2989 0.0785 2.1516 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8165 0.4780 1.0828 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3684 0.3780 0.8757 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8136 0.7989 -0.2404 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3839 0.7332 -0.5197 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8761 1.2586 -1.7154 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5307 1.2067 -1.9984 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0463 1.7353 -3.1958 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9204 2.3223 -4.1160 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6175 0.6414 -1.1324 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0940 0.1184 0.0456 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4571 0.1743 0.3275 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9175 -0.4333 0.7610 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9877 -0.2159 2.2596 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1067 -0.8297 2.7552 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7799 0.3367 0.1450 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2113 0.4778 -1.1999 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4549 -0.2573 0.3062 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8421 -1.1089 -0.5535 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5937 -1.6233 -0.2694 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0260 -2.4816 -1.1757 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6957 -2.8281 -2.3585 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8885 -1.3125 0.8933 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -0.4325 1.7671 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7817 0.0740 1.4756 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8693 -0.0990 2.9416 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5167 0.7884 3.8380 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6585 -1.8148 1.1685 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5911 -1.2322 1.1422 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1553 -1.3061 -0.2910 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4919 -0.6359 -0.3263 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6092 -1.3873 -0.6107 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8550 -0.7395 -0.6185 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9821 0.6045 -0.3524 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8235 1.3252 -0.0697 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6155 0.7102 -0.0604 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9212 2.6667 0.1994 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8623 3.5230 0.4977 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1491 1.2983 -0.3415 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4520 0.8222 -0.6097 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3641 1.0020 0.5700 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6962 0.3633 0.3830 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6139 0.5967 1.4077 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8665 0.0436 1.3679 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2643 -0.7532 0.3291 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3484 -0.9787 -0.6811 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0615 -0.4219 -0.6572 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7591 -1.7883 -1.7369 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8367 -2.0204 -2.7798 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5490 -1.3164 0.2934 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8610 0.3988 1.7477 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9391 1.7581 -1.7441 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8886 3.0501 -1.1992 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2887 -0.5457 -1.0681 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5291 -1.9442 2.0632 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6935 -3.2851 1.7203 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4161 0.8908 0.3128 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7449 -0.0484 1.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4740 1.2191 -0.9954 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6103 1.6935 -2.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8678 1.7547 -4.2517 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1615 3.3750 -3.8347 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4296 2.3797 -5.1306 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8072 -0.2527 1.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7671 -1.5118 0.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8883 0.8364 2.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0898 -0.7585 2.6711 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9989 -1.8098 2.8362 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8247 1.3576 0.6313 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3725 -1.3669 -1.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0354 -3.5835 -2.8711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7934 -1.9373 -3.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6915 -3.3086 -2.1664 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2263 0.7535 2.2021 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5109 0.3210 4.0545 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7065 1.7638 3.3288 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8995 0.9213 4.7527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5469 -0.1180 1.3032 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1798 -2.3382 -0.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5270 -2.4404 -0.8200 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7421 -1.3159 -0.8406 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 1.2347 0.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2113 4.5585 0.7515 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1486 3.6010 -0.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2838 3.1679 1.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3908 -0.2143 -0.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4608 2.0807 0.7846 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3742 1.2230 2.2685 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5749 0.2372 2.1867 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3798 -0.6315 -1.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2655 -2.5641 -3.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4434 -1.0465 -3.1559 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9826 -2.6463 -2.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6747 -2.2207 0.7693 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5280 -0.5281 1.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9388 1.5388 -2.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1832 1.7374 -2.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1172 3.1761 -0.5938 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1068 0.1529 -0.4643 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2060 -1.9153 3.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5697 -1.5173 2.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0455 -3.8720 2.1826 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 7 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 16 17 1 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 23 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 1 0 34 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 1 0 45 50 1 0 41 51 1 0 40 52 1 0 52 53 1 0 30 54 1 0 29 55 1 0 55 56 1 0 12 5 1 0 25 18 1 0 36 31 1 0 47 42 1 0 17 10 1 0 2 57 1 0 3 58 1 0 4 59 1 0 6 60 1 0 9 61 1 0 9 62 1 0 9 63 1 0 12 64 1 0 13 65 1 1 14 66 1 0 14 67 1 0 15 68 1 0 16 69 1 1 19 70 1 0 22 71 1 0 22 72 1 0 22 73 1 0 25 74 1 0 27 75 1 0 27 76 1 0 27 77 1 0 29 78 1 0 30 79 1 0 32 80 1 0 33 81 1 0 36 82 1 0 38 83 1 0 38 84 1 0 38 85 1 0 40 86 1 0 41 87 1 0 43 88 1 0 44 89 1 0 47 90 1 0 49 91 1 0 49 92 1 0 49 93 1 0 50 94 1 0 51 95 1 0 52 96 1 0 52 97 1 0 53 98 1 0 54 99 1 0 55100 1 0 55101 1 0 56102 1 0 M END

Standard InCHIKey	HITLEOURIXKLBL-DRATVDAASA-N
Standard InCHI	InChI=1S/C41H46O15/c1-49-30-15-23(8-10-28(30)46)37(47)35(20-44)54-29-11-9-24(16-31(29)50-2)38(48)36(21-45)55-41-33(52-4)17-25(18-34(41)53-5)39-27(19-43)26-13-22(7-6-12-42)14-32(51-3)40(26)56-39/h6-18,27,35-39,43-48H,19-21H2,1-5H3/b7-6+/t27-,35?,36?,37?,38?,39+/m1/s1
SMILES	O=C/C=C/c1cc(OC)c2c(c1)[C@@H](CO)[C@@H](O2)c1cc(OC)c(c(c1)OC)OC(C(c1ccc(c(c1)OC)OC(C(c1ccc(c(c1)OC)O)O)CO)O)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	778.28	Volume:	769.853 ? Van der Waals volume.
Dense:	1.011	LogP:	1.959 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.38 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.557 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	30.0
TPSA:	212.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.059	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.901	Fsp³:	0.341
MCE-18:	107.545 ? 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:	0.529	Fluc inhibitor:	0.431 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.067 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.522 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.232	Promiscuous compounds:	0.029

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.191	MDCK Permeability:	-4.955
Pgp-inhibitor:	0.0	Pgp-substrate:	0.007
PAMPA:	0.683 ? 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):	0.029
20% Bioavailability (F20%):	0.329	30% Bioavailability (F30%):	0.762
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.233
Plasma Protein Binding (PPB):	74.47%	Volume Distribution (VD):	-0.12
Fu:	26.383% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.691
BSEP inhibitor:	0.48

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.911	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.768
CYP2D6-inhibitor:	0.349	CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.143	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.002 ? 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):

5.29

Half-life (T1/2):

2.521

ADMET: Toxicity

hERG Blockers:	0.093	hERG Blockers (10um):	0.213
Human Hepatotoxicity (H-HT):	0.836	Drug-induced Liver Injury (DILI):	0.425
AMES Toxicity:	0.437	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.803	Skin Sensitization:	0.16
Carcinogencity:	0.534	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.093
Drug-induced Neurotoxicity:	0.463	Ototoxicity:	0.997
Hematotoxicity:	0.163	Drug-induced Nephrotoxicity:	0.975
Genotoxicity:	0.704	RPMI-8226 Immunitoxicity:	0.377
A549 Cytotoxicity:	0.15	Hek293 Cytotoxicity:	0.617
BCF:	0.889 ? 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:	3.62 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.442 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.573 ? 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
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792422]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17343407]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14922	Tarenna attenuata	Species	Rubiaceae	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
Activity	4
IC50	1

Activity Type	# Activity
Cell line	4
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
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	52.8	%	PMID[23186727]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	47.9	%	PMID[10425121]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	64.4	%	PubChem BioAssay data set
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	55.9	%	PMID[18183025]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	201000.0	nM	PMID[18183025]

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 NPC470827 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	25986
0.1-0.2	21426
0.2-0.3	2167
0.3-0.4	174
0.4-0.5	64
0.5-0.6	23
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC470828
0.92	High Similarity	NPC470769
0.7975	Intermediate Similarity	NPC260397
0.7037	Intermediate Similarity	NPC43065
0.6623	Remote Similarity	NPC284881
0.6623	Remote Similarity	NPC93433
0.6623	Remote Similarity	NPC474444
0.6579	Remote Similarity	NPC267291
0.6494	Remote Similarity	NPC476387
0.6494	Remote Similarity	NPC237594
0.6494	Remote Similarity	NPC119060
0.6162	Remote Similarity	NPC485396
0.6162	Remote Similarity	NPC485394
0.6162	Remote Similarity	NPC485395
0.6047	Remote Similarity	NPC181615
0.5949	Remote Similarity	NPC473408
0.5556	Remote Similarity	NPC147821
0.5556	Remote Similarity	NPC319625
0.5556	Remote Similarity	NPC156502
0.5556	Remote Similarity	NPC10737
0.5556	Remote Similarity	NPC183181
0.5556	Remote Similarity	NPC41706
0.55	Remote Similarity	NPC7903
0.55	Remote Similarity	NPC160991
0.5476	Remote Similarity	NPC206413
0.5476	Remote Similarity	NPC482649
0.5476	Remote Similarity	NPC149003
0.5476	Remote Similarity	NPC471414
0.5476	Remote Similarity	NPC482647
0.5476	Remote Similarity	NPC482648
0.5476	Remote Similarity	NPC482651
0.5476	Remote Similarity	NPC194244
0.5476	Remote Similarity	NPC482650
0.5294	Remote Similarity	NPC253878
0.5238	Remote Similarity	NPC224876
0.5185	Remote Similarity	NPC601893
0.5172	Remote Similarity	NPC163898
0.5122	Remote Similarity	NPC26394

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4884
0.1-0.2	4202
0.2-0.3	61
0.3-0.4	3
0.4-0.5	0
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