NPASS Compound

Natural Product: NPC255423

Natural Product ID	NPC255423
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	POMAQDQEVHXLGT-XRMLUXEKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	91885271
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 96101 0 0 0 0 0 0 0 0999 V2000 6.0795 0.6414 -3.3206 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5330 -0.4606 -2.4698 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6725 -1.3344 -1.9890 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0405 -2.4483 -1.1806 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1507 -1.9123 -0.0888 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1375 -0.9831 -0.7307 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3113 -0.3894 0.1855 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9682 -0.5781 0.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4769 -0.0210 -1.2923 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8550 1.4339 -1.4347 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5619 2.2212 -1.5772 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3015 1.8417 -0.3666 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6536 0.4094 -0.4649 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1191 -0.2184 -1.5037 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9902 0.1969 -0.9111 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5160 -1.0556 -1.0798 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3237 -1.6284 -2.3610 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7200 -1.0116 -3.2588 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8197 -2.8890 -2.5994 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6377 -3.4596 -3.8463 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1217 -4.7173 -4.1117 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7870 -5.3922 -3.1167 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9931 -4.8707 -1.8664 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4931 -3.5874 -1.6127 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6409 -3.0271 -0.4765 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1829 -1.7913 -0.1668 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4467 -1.3190 1.1809 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3132 -0.0444 1.6325 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5537 0.2943 2.9705 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9358 -0.6543 3.8797 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0799 -1.9509 3.4529 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8398 -2.2582 2.1430 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4662 -2.9057 4.3758 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6402 -4.2713 4.0289 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1739 -0.3002 5.2201 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2778 -6.6658 -3.3844 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9497 -2.7092 -4.8081 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3703 2.6835 -0.2197 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3144 3.5874 0.8085 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6925 4.9901 0.4931 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7134 5.7814 1.7822 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2127 5.0175 2.9659 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8004 3.6305 3.0561 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7609 2.6662 3.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2254 3.1735 1.8077 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1959 4.9941 3.0409 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8685 6.8991 1.5753 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9266 5.6210 -0.4735 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9126 3.5403 -1.6206 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6047 1.9435 -0.4125 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8575 0.0263 -1.3735 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8594 -1.2001 0.8703 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0345 -3.2832 -0.7326 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6170 -0.6334 -1.2781 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1508 0.2904 -4.3823 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1136 0.9408 -3.0303 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4668 1.5500 -3.3294 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8796 -1.1041 -3.0957 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1325 -1.7898 -2.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3870 -3.0088 -1.8818 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6730 -2.7717 0.4090 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6461 -1.5680 -1.5184 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6525 -1.6398 0.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4732 -0.0765 0.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9903 -0.5756 -2.1021 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4111 1.6204 -2.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0071 1.9303 -2.4723 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3825 2.0582 0.5074 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4758 -0.2127 0.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9701 -5.1552 -5.1023 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5042 -5.3598 -1.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0425 0.7357 0.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4533 1.3030 3.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9612 -3.2932 1.8318 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2377 -4.3862 3.0999 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1819 -4.7589 4.8547 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6499 -4.7814 3.9025 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9833 -0.9813 5.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9222 -6.7393 -4.1832 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0604 -3.1111 -5.1277 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3308 3.5185 1.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7817 4.9413 0.1629 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 6.2247 1.9813 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5254 5.5692 3.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6554 3.6596 3.7526 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1487 2.1587 4.4851 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5509 1.8403 2.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2049 3.1515 3.7859 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5893 5.7585 2.5297 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1007 7.3895 0.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5264 6.2598 -0.9387 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5448 4.0292 -2.4242 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3637 1.7075 0.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8664 -1.6835 1.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6314 -4.1603 -0.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9866 -1.1017 -0.5088 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 30 35 1 0 22 36 1 0 20 37 1 0 12 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 43 45 1 0 42 46 1 0 41 47 1 0 40 48 1 0 11 49 1 0 10 50 1 0 6 51 1 0 5 52 1 0 4 53 1 0 3 54 1 0 51 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 45 39 1 0 24 19 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 6 3 59 1 6 4 60 1 6 5 61 1 1 6 62 1 6 8 63 1 0 8 64 1 0 9 65 1 6 10 66 1 6 11 67 1 6 12 68 1 1 13 69 1 0 21 70 1 0 23 71 1 0 28 72 1 0 29 73 1 0 32 74 1 0 34 75 1 0 34 76 1 0 34 77 1 0 35 78 1 0 36 79 1 0 37 80 1 0 39 81 1 1 40 82 1 6 41 83 1 1 42 84 1 1 43 85 1 1 44 86 1 0 44 87 1 0 44 88 1 0 46 89 1 0 47 90 1 0 48 91 1 0 49 92 1 0 50 93 1 0 52 94 1 0 53 95 1 0 54 96 1 0 M END

Standard InCHIKey	POMAQDQEVHXLGT-XRMLUXEKSA-N
Standard InCHI	InChI=1S/C34H42O20/c1-10-20(38)24(42)27(45)32(49-10)48-9-18-22(40)26(44)31(54-33-28(46)25(43)21(39)11(2)50-33)34(52-18)53-30-23(41)19-15(37)7-13(35)8-17(19)51-29(30)12-4-5-14(36)16(6-12)47-3/h4-8,10-11,18,20-22,24-28,31-40,42-46H,9H2,1-3H3/t10-,11-,18+,20+,21+,22-,24+,25+,26-,27+,28+,31+,32-,33-,34?/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(O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)OC)O)O)O)O[C@H]2[C@@H]([C@@H]([C@@H]([C@H](C)O2)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	770.23	Volume:	699.994 ? Van der Waals volume.
Dense:	1.1	LogP:	0.227 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.673 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.634 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	317.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.107	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.378	Fsp³:	0.559
MCE-18:	153.34 ? 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:	0.611	Fluc inhibitor:	0.254 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.667 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.577 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.204	Promiscuous compounds:	0.366

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.481	MDCK Permeability:	-5.251
Pgp-inhibitor:	0.0	Pgp-substrate:	0.995
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):	0.002
20% Bioavailability (F20%):	0.043	30% Bioavailability (F30%):	0.196
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.067
Plasma Protein Binding (PPB):	78.961%	Volume Distribution (VD):	-0.156
Fu:	19.888% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.628
OATP1B3 inhibitor:	0.588	BCRP inhibitor:	0.03
BSEP inhibitor:	0.963

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:	0.005
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.299 ? 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):

0.886

Half-life (T1/2):

6.287

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.423
Human Hepatotoxicity (H-HT):	0.074	Drug-induced Liver Injury (DILI):	0.042
AMES Toxicity:	0.702	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.029	Skin Sensitization:	0.834
Carcinogencity:	0.006	Eye Corrosion:	0.0
Eye Irritation:	0.197	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.988
Hematotoxicity:	0.081	Drug-induced Nephrotoxicity:	0.099
Genotoxicity:	0.012	RPMI-8226 Immunitoxicity:	0.179
A549 Cytotoxicity:	0.219	Hek293 Cytotoxicity:	0.452
BCF:	0.443 ? 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:	3.13 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.717 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.786 ? 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
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28251	Typha orientalis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28251	Typha orientalis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9822	Typha angustifolia	Species	Typhaceae	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 NPC255423 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	19306
0.1-0.2	26606
0.2-0.3	3078
0.3-0.4	464
0.4-0.5	192
0.5-0.6	114
0.6-0.7	61
0.7-0.8	0
0.8-0.85	7
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC89052
0.9121	High Similarity	NPC173837
0.8539	High Similarity	NPC12013
0.8539	High Similarity	NPC11432
0.8539	High Similarity	NPC477613
0.8444	Intermediate Similarity	NPC122467
0.8261	Intermediate Similarity	NPC476472
0.8261	Intermediate Similarity	NPC294815
0.8261	Intermediate Similarity	NPC16194
0.8261	Intermediate Similarity	NPC220173
0.8085	Intermediate Similarity	NPC602448
0.8039	Intermediate Similarity	NPC192539
0.7979	Intermediate Similarity	NPC221342
0.7979	Intermediate Similarity	NPC476470
0.7684	Intermediate Similarity	NPC89127
0.75	Intermediate Similarity	NPC303694
0.7396	Intermediate Similarity	NPC142142
0.7339	Intermediate Similarity	NPC473554
0.7253	Intermediate Similarity	NPC476215
0.7174	Intermediate Similarity	NPC95866
0.7143	Intermediate Similarity	NPC223747
0.7143	Intermediate Similarity	NPC480445
0.7113	Intermediate Similarity	NPC473327
0.7071	Intermediate Similarity	NPC292929
0.7009	Intermediate Similarity	NPC480444
0.6947	Remote Similarity	NPC173582
0.6947	Remote Similarity	NPC265885
0.6947	Remote Similarity	NPC181465
0.6947	Remote Similarity	NPC215710
0.6947	Remote Similarity	NPC163242
0.6947	Remote Similarity	NPC272068
0.6947	Remote Similarity	NPC473438
0.6947	Remote Similarity	NPC253788
0.6916	Remote Similarity	NPC162394
0.6907	Remote Similarity	NPC153755
0.6875	Remote Similarity	NPC203259
0.6875	Remote Similarity	NPC33054
0.6875	Remote Similarity	NPC155877
0.6875	Remote Similarity	NPC176740
0.6875	Remote Similarity	NPC471725
0.6875	Remote Similarity	NPC134532
0.6875	Remote Similarity	NPC602582
0.6838	Remote Similarity	NPC487501
0.6752	Remote Similarity	NPC487500
0.6731	Remote Similarity	NPC219043
0.6637	Remote Similarity	NPC487499
0.6552	Remote Similarity	NPC487502
0.6509	Remote Similarity	NPC25523
0.6429	Remote Similarity	NPC39834
0.6355	Remote Similarity	NPC480441
0.6354	Remote Similarity	NPC203050
0.6354	Remote Similarity	NPC170052
0.6354	Remote Similarity	NPC225434
0.6354	Remote Similarity	NPC135846
0.6339	Remote Similarity	NPC209550
0.6289	Remote Similarity	NPC254855
0.6289	Remote Similarity	NPC94610
0.6273	Remote Similarity	NPC488734
0.6273	Remote Similarity	NPC488735
0.6273	Remote Similarity	NPC488739
0.6273	Remote Similarity	NPC488732
0.6273	Remote Similarity	NPC488738
0.6226	Remote Similarity	NPC203145
0.62	Remote Similarity	NPC304741
0.6174	Remote Similarity	NPC25946
0.6168	Remote Similarity	NPC473072
0.6161	Remote Similarity	NPC488740
0.6161	Remote Similarity	NPC488736
0.6161	Remote Similarity	NPC488733
0.6139	Remote Similarity	NPC255157
0.6139	Remote Similarity	NPC470444
0.6139	Remote Similarity	NPC259896
0.6139	Remote Similarity	NPC473571
0.6139	Remote Similarity	NPC110941
0.6121	Remote Similarity	NPC21359
0.6121	Remote Similarity	NPC460984
0.61	Remote Similarity	NPC470405
0.6078	Remote Similarity	NPC126784
0.6078	Remote Similarity	NPC240306
0.6078	Remote Similarity	NPC241423
0.6055	Remote Similarity	NPC217520
0.6053	Remote Similarity	NPC488737
0.6042	Remote Similarity	NPC219904
0.604	Remote Similarity	NPC156869
0.6	Remote Similarity	NPC480443
0.6	Remote Similarity	NPC471079
0.5963	Remote Similarity	NPC48984
0.595	Remote Similarity	NPC249560
0.5948	Remote Similarity	NPC480442
0.5946	Remote Similarity	NPC139571
0.5941	Remote Similarity	NPC67326
0.5938	Remote Similarity	NPC216496
0.5882	Remote Similarity	NPC231787
0.5872	Remote Similarity	NPC189564
0.5851	Remote Similarity	NPC111929
0.5851	Remote Similarity	NPC320283
0.5851	Remote Similarity	NPC41121
0.5842	Remote Similarity	NPC609888
0.5818	Remote Similarity	NPC292019
0.5818	Remote Similarity	NPC202908
0.5789	Remote Similarity	NPC127546
0.5789	Remote Similarity	NPC57625
0.5789	Remote Similarity	NPC173637
0.5789	Remote Similarity	NPC317489
0.5789	Remote Similarity	NPC223424
0.5789	Remote Similarity	NPC600591
0.5785	Remote Similarity	NPC30011
0.5785	Remote Similarity	NPC72554
0.575	Remote Similarity	NPC275977
0.5729	Remote Similarity	NPC265530
0.5728	Remote Similarity	NPC65563
0.5728	Remote Similarity	NPC470949
0.5728	Remote Similarity	NPC605592
0.5714	Remote Similarity	NPC470443
0.5701	Remote Similarity	NPC76831
0.5686	Remote Similarity	NPC187379
0.5673	Remote Similarity	NPC186816
0.5644	Remote Similarity	NPC116864
0.5644	Remote Similarity	NPC244776
0.5641	Remote Similarity	NPC241781
0.5632	Remote Similarity	NPC279989
0.56	Remote Similarity	NPC97817
0.5596	Remote Similarity	NPC218161
0.5556	Remote Similarity	NPC195257
0.5556	Remote Similarity	NPC471669
0.5517	Remote Similarity	NPC198199
0.5514	Remote Similarity	NPC32641
0.5514	Remote Similarity	NPC256188
0.55	Remote Similarity	NPC224530
0.5495	Remote Similarity	NPC11468
0.547	Remote Similarity	NPC156785
0.547	Remote Similarity	NPC474522
0.5463	Remote Similarity	NPC97119
0.5463	Remote Similarity	NPC603079
0.5398	Remote Similarity	NPC477895
0.5378	Remote Similarity	NPC120952
0.5377	Remote Similarity	NPC35167
0.537	Remote Similarity	NPC482026
0.537	Remote Similarity	NPC35119
0.5361	Remote Similarity	NPC135599
0.5361	Remote Similarity	NPC73855
0.5361	Remote Similarity	NPC113968
0.5361	Remote Similarity	NPC328940
0.5361	Remote Similarity	NPC277174
0.5361	Remote Similarity	NPC606877
0.5351	Remote Similarity	NPC473644
0.5347	Remote Similarity	NPC120099
0.5347	Remote Similarity	NPC609478
0.5333	Remote Similarity	NPC175429
0.5327	Remote Similarity	NPC488073
0.5327	Remote Similarity	NPC488074
0.5304	Remote Similarity	NPC311850
0.53	Remote Similarity	NPC325555
0.53	Remote Similarity	NPC226304
0.5273	Remote Similarity	NPC470447
0.5254	Remote Similarity	NPC298666
0.5248	Remote Similarity	NPC60735
0.5248	Remote Similarity	NPC175107
0.5248	Remote Similarity	NPC26230
0.5238	Remote Similarity	NPC139320
0.5225	Remote Similarity	NPC470445
0.5196	Remote Similarity	NPC101026
0.5196	Remote Similarity	NPC259957
0.5196	Remote Similarity	NPC488077
0.5189	Remote Similarity	NPC471748
0.5169	Remote Similarity	NPC68592
0.5152	Remote Similarity	NPC77672
0.5152	Remote Similarity	NPC133671
0.5152	Remote Similarity	NPC135391
0.5152	Remote Similarity	NPC78263
0.5152	Remote Similarity	NPC250069
0.5149	Remote Similarity	NPC472459
0.5143	Remote Similarity	NPC473682
0.5135	Remote Similarity	NPC85751
0.5135	Remote Similarity	NPC473073
0.5135	Remote Similarity	NPC473071
0.5135	Remote Similarity	NPC19240
0.5133	Remote Similarity	NPC14187
0.5126	Remote Similarity	NPC470713
0.5113	Remote Similarity	NPC33083
0.51	Remote Similarity	NPC145038
0.51	Remote Similarity	NPC56077
0.51	Remote Similarity	NPC281131
0.51	Remote Similarity	NPC253662
0.51	Remote Similarity	NPC179950
0.51	Remote Similarity	NPC88789
0.51	Remote Similarity	NPC491374
0.5098	Remote Similarity	NPC48093
0.5094	Remote Similarity	NPC258044
0.5094	Remote Similarity	NPC217387
0.5094	Remote Similarity	NPC29958
0.5093	Remote Similarity	NPC129264
0.5089	Remote Similarity	NPC287889
0.5089	Remote Similarity	NPC470449
0.5052	Remote Similarity	NPC54802
0.5052	Remote Similarity	NPC197304
0.505	Remote Similarity	NPC305811
0.505	Remote Similarity	NPC46420
0.5046	Remote Similarity	NPC470125
0.5044	Remote Similarity	NPC470446

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC255423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5609
0.1-0.2	3494
0.2-0.3	38
0.3-0.4	4
0.4-0.5	2
0.5-0.6	2
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
0.6875	Remote Similarity	NPD6797	Phase 2
0.5273	Remote Similarity	NPD7251	Phase 2
0.5221	Remote Similarity	NPD7808	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