NPASS Compound

Natural Product: NPC134340

Natural Product ID	NPC134340
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XQQFUXJSLVWQSS-UOMQSTFGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44257901
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 94 99 0 0 0 0 0 0 0 0999 V2000 -2.6182 -4.0874 0.8172 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5847 -3.3183 -0.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9695 -3.8886 -0.0511 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2481 -4.7695 -1.2426 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8222 -4.0944 -2.5526 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1165 -2.8275 -2.1638 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5819 -2.1139 -3.2055 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9704 -0.8005 -3.2728 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5737 0.0201 -2.0675 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 1.4058 -2.2550 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4873 2.3934 -1.2731 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0160 2.2352 -1.4193 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6928 0.8058 -0.9747 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3360 0.5828 -0.8582 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3343 0.0879 0.2413 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3166 -0.2560 1.4028 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3773 -0.7552 2.5027 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7335 -0.9040 2.4195 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4332 -1.3997 3.5049 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8249 -1.7106 4.5615 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8022 -1.5315 3.3693 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4668 -1.1915 2.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9154 -1.3393 2.0929 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7299 -1.8282 3.0782 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1120 -1.9467 2.9067 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7043 -1.5689 1.7220 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8964 -1.0723 0.7140 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5313 -0.9656 0.9106 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0755 -1.6903 1.5625 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7455 -1.3242 0.3836 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7484 -0.7236 1.2106 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4408 -0.5763 1.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7191 -0.0867 0.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3181 -1.0927 3.6630 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1928 -0.0155 -1.9859 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2222 3.1494 -0.7736 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2979 3.8165 -1.5285 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5012 5.2797 -1.3798 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5410 5.5518 0.1077 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3180 4.6066 0.8614 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3418 3.8488 0.1050 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6968 4.5726 0.1410 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0037 3.4321 -1.1635 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4341 3.7244 1.6729 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8774 5.3199 0.5115 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7214 5.6425 -1.9185 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9678 3.6459 -1.5437 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5045 1.3437 -2.1058 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0405 -3.2140 -1.3339 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9822 -4.9914 -3.2064 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5669 -5.9633 -1.0448 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1179 -4.6733 1.0913 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6924 -5.1638 0.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9067 -3.9971 1.8813 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5966 -3.7220 0.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6565 -2.2767 0.3866 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7580 -3.0944 0.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3382 -4.9743 -1.2447 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7275 -3.9354 -3.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8096 -2.2272 -1.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4576 -0.3702 -4.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0607 -0.6752 -3.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9624 -0.4544 -1.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8397 1.7542 -3.2686 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8328 2.0962 -0.2355 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7506 2.2504 -2.4946 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3124 0.6105 -0.0821 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3743 -0.1523 1.4985 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3296 -1.9214 4.2312 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2965 -2.1355 4.0235 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7135 -2.3400 3.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3803 -0.7855 -0.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8976 -0.5734 0.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2208 -1.6261 -0.5231 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7645 -1.7783 0.3956 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9111 -0.2148 0.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2435 0.1785 -0.6857 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1555 -0.4612 4.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4004 3.5196 -2.5835 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2618 5.8976 -1.8954 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3604 6.6140 0.3431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8834 5.2306 1.6190 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5446 2.8993 0.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9895 4.7567 1.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4961 3.9775 -0.2993 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5845 5.5864 -0.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2129 3.3511 2.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4764 6.0430 0.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8475 5.3802 -2.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7972 3.7964 -1.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6965 1.0492 -1.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3020 -5.9006 -2.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1772 -6.7233 -1.0722 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6487 -4.2322 1.7999 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 26 29 1 0 29 30 1 0 22 31 1 0 31 32 1 0 32 33 2 0 17 34 1 0 13 35 1 0 12 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 40 44 1 0 39 45 1 0 38 46 1 0 11 47 1 0 10 48 1 0 6 49 1 0 5 50 1 0 4 51 1 0 3 52 1 0 49 2 1 0 35 9 1 0 43 37 1 0 33 15 1 0 32 18 1 0 28 23 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 0 3 57 1 1 4 58 1 0 5 59 1 6 6 60 1 1 8 61 1 0 8 62 1 0 9 63 1 0 10 64 1 6 11 65 1 1 12 66 1 0 13 67 1 1 16 68 1 0 21 69 1 0 24 70 1 0 25 71 1 0 27 72 1 0 28 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 33 77 1 0 34 78 1 0 37 79 1 6 38 80 1 6 39 81 1 0 40 82 1 1 41 83 1 0 42 84 1 0 42 85 1 0 42 86 1 0 44 87 1 0 45 88 1 0 46 89 1 0 47 90 1 0 48 91 1 0 50 92 1 0 51 93 1 0 52 94 1 0 M END

Standard InCHIKey	XQQFUXJSLVWQSS-UOMQSTFGSA-N
Standard InCHI	InChI=1S/C34H42O18/c1-12-23(37)26(40)29(43)32(47-12)46-11-21-25(39)28(42)31(52-33-30(44)27(41)24(38)13(2)48-33)34(51-21)49-16-8-17(35)22-18(36)10-19(50-20(22)9-16)14-4-6-15(45-3)7-5-14/h4-10,12-13,21,23-35,37-44H,11H2,1-3H3/t12?,13?,21?,23-,24-,25+,26?,27?,28-,29-,30-,31?,32+,33-,34+/m0/s1
SMILES	CC1[C@@H](C([C@@H]([C@H](OCC2[C@H]([C@@H](C([C@H](Oc3cc(c4c(=O)cc(c5ccc(cc5)OC)oc4c3)O)O2)O[C@H]2[C@H](C([C@H](C(C)O2)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	738.24	Volume:	682.414 ? Van der Waals volume.
Dense:	1.082	LogP:	0.844 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.499 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.3 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	276.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.115	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.212	Fsp³:	0.559
MCE-18:	146.208 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.646	Fluc inhibitor:	0.244 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.953 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.863 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.226	Promiscuous compounds:	0.199

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.39	MDCK Permeability:	-5.261
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.999
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.841
Plasma Protein Binding (PPB):	83.157%	Volume Distribution (VD):	-0.163
Fu:	15.997% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.842
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.339
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:	0.998
HLM stability:	0.127 ? 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):

0.643

Half-life (T1/2):

2.984

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.101
Human Hepatotoxicity (H-HT):	0.722	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.993	Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.235	Skin Sensitization:	0.994
Carcinogencity:	0.262	Eye Corrosion:	0.0
Eye Irritation:	0.029	Respiratory Toxicity:	0.167
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.956
Hematotoxicity:	0.454	Drug-induced Nephrotoxicity:	0.783
Genotoxicity:	0.97	RPMI-8226 Immunitoxicity:	0.474
A549 Cytotoxicity:	0.969	Hek293 Cytotoxicity:	0.904
BCF:	0.392 ? 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:	3.166 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.888 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.001 ? 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
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flowers	bought from a drugstore in Beijing	n.a.	PMID[10514305]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[14738377]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flowers	n.a.	n.a.	PMID[21524582]
NPO6361	Turpinia arguta	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6361	Turpinia arguta	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	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 NPC134340 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	15419
0.1-0.2	29751
0.2-0.3	3747
0.3-0.4	582
0.4-0.5	248
0.5-0.6	66
0.6-0.7	16
0.7-0.8	1
0.8-0.85	6
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9302	High Similarity	NPC11468
0.8989	High Similarity	NPC473644
0.8889	High Similarity	NPC311850
0.8602	High Similarity	NPC68592
0.8353	Intermediate Similarity	NPC22062
0.8353	Intermediate Similarity	NPC473634
0.8353	Intermediate Similarity	NPC138811
0.8021	Intermediate Similarity	NPC488086
0.8	Intermediate Similarity	NPC488087
0.8	Intermediate Similarity	NPC488083
0.7938	Intermediate Similarity	NPC198199
0.79	Intermediate Similarity	NPC262222
0.7755	Intermediate Similarity	NPC298666
0.77	Intermediate Similarity	NPC120952
0.7391	Intermediate Similarity	NPC209296
0.7222	Intermediate Similarity	NPC44931
0.72	Intermediate Similarity	NPC488088
0.7143	Intermediate Similarity	NPC65003
0.7128	Intermediate Similarity	NPC142142
0.7053	Intermediate Similarity	NPC475382
0.7021	Intermediate Similarity	NPC473623
0.6957	Remote Similarity	NPC210073
0.6947	Remote Similarity	NPC488089
0.6882	Remote Similarity	NPC204693
0.6882	Remote Similarity	NPC115674
0.6875	Remote Similarity	NPC195257
0.6771	Remote Similarity	NPC479766
0.6556	Remote Similarity	NPC80188
0.6408	Remote Similarity	NPC480441
0.6408	Remote Similarity	NPC25523
0.6404	Remote Similarity	NPC181712
0.6292	Remote Similarity	NPC95090
0.6292	Remote Similarity	NPC27408
0.6289	Remote Similarity	NPC46202
0.6277	Remote Similarity	NPC8856
0.6139	Remote Similarity	NPC101636
0.6067	Remote Similarity	NPC331652
0.5979	Remote Similarity	NPC67105
0.5922	Remote Similarity	NPC135358
0.59	Remote Similarity	NPC12013
0.59	Remote Similarity	NPC11432
0.59	Remote Similarity	NPC477613
0.5842	Remote Similarity	NPC122467
0.5842	Remote Similarity	NPC483707
0.5824	Remote Similarity	NPC19709
0.5816	Remote Similarity	NPC227508
0.581	Remote Similarity	NPC89052
0.5804	Remote Similarity	NPC209550
0.58	Remote Similarity	NPC240306
0.5714	Remote Similarity	NPC473043
0.57	Remote Similarity	NPC122809
0.57	Remote Similarity	NPC186816
0.5673	Remote Similarity	NPC298171
0.567	Remote Similarity	NPC211594
0.5644	Remote Similarity	NPC475366
0.5638	Remote Similarity	NPC27942
0.5625	Remote Similarity	NPC220169
0.5625	Remote Similarity	NPC29353
0.5619	Remote Similarity	NPC602448
0.5588	Remote Similarity	NPC65711
0.5545	Remote Similarity	NPC257566
0.5524	Remote Similarity	NPC221342
0.5524	Remote Similarity	NPC476470
0.5521	Remote Similarity	NPC22832
0.5521	Remote Similarity	NPC243930
0.549	Remote Similarity	NPC64051
0.5464	Remote Similarity	NPC607707
0.5429	Remote Similarity	NPC479765
0.5429	Remote Similarity	NPC89127
0.5413	Remote Similarity	NPC173837
0.5408	Remote Similarity	NPC190003
0.54	Remote Similarity	NPC295613
0.54	Remote Similarity	NPC187379
0.54	Remote Similarity	NPC473657
0.5385	Remote Similarity	NPC32641
0.5385	Remote Similarity	NPC256188
0.5385	Remote Similarity	NPC229409
0.5361	Remote Similarity	NPC608742
0.5333	Remote Similarity	NPC270675
0.5333	Remote Similarity	NPC195685
0.5327	Remote Similarity	NPC253685
0.5319	Remote Similarity	NPC39360
0.5319	Remote Similarity	NPC29763
0.5319	Remote Similarity	NPC210003
0.53	Remote Similarity	NPC239549
0.5294	Remote Similarity	NPC303913
0.5273	Remote Similarity	NPC472993
0.5238	Remote Similarity	NPC482026
0.5238	Remote Similarity	NPC35119
0.5225	Remote Similarity	NPC303694
0.5185	Remote Similarity	NPC472994
0.5152	Remote Similarity	NPC311830
0.5138	Remote Similarity	NPC14187
0.5124	Remote Similarity	NPC473554
0.5104	Remote Similarity	NPC189142
0.5104	Remote Similarity	NPC77660
0.5102	Remote Similarity	NPC611303
0.5094	Remote Similarity	NPC473327
0.5053	Remote Similarity	NPC14606
0.5052	Remote Similarity	NPC186807
0.5052	Remote Similarity	NPC273932
0.505	Remote Similarity	NPC172807
0.5049	Remote Similarity	NPC275454

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC134340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4495
0.1-0.2	4564
0.2-0.3	80
0.3-0.4	5
0.4-0.5	2
0.5-0.6	3
0.6-0.7	0
0.7-0.8	1
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
0.7391	Intermediate Similarity	NPD7054	Phase 4
0.5514	Remote Similarity	NPD7472	Pre-clinical
0.537	Remote Similarity	NPD7808	Phase 3
0.5283	Remote Similarity	NPD7251	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