NPASS Compound

Natural Product: NPC289897

Natural Product ID	NPC289897
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WDAWHSXOXNKHHI-MQDLSUFXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6325156
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 99105 0 0 0 0 0 0 0 0999 V2000 3.4773 -2.2621 -0.7114 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5637 -1.2561 -1.0140 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3448 -0.9009 0.2218 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5008 -0.0206 1.0991 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0759 1.1800 0.2951 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1696 0.6038 -0.8167 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0251 -0.1226 -1.6146 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1945 -0.0545 -0.1740 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9136 0.3971 -0.2384 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0853 -0.5012 -0.8563 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0084 -1.1793 0.0978 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7977 -0.1995 0.9691 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7448 -0.8570 2.3659 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 -2.0983 2.3756 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2315 -0.1188 0.5497 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2456 -0.3023 1.6201 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5337 0.4694 1.4006 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9990 0.5311 -0.0024 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2017 1.4714 -0.0413 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3917 -0.7103 -0.6725 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3280 -0.3383 -2.1378 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0680 0.5021 -2.2033 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9138 1.1429 -0.8290 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5281 1.0695 -0.3288 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0012 2.3590 0.2627 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4735 2.2059 0.2222 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0879 1.0904 1.1211 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4086 0.8830 1.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3440 1.5851 2.4310 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1824 2.5205 -1.0283 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6984 -1.3056 -0.2943 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6430 -1.4646 -1.2038 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8143 -2.0624 -0.5952 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9223 -2.3641 -1.1563 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5153 -2.2506 0.7205 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2292 -1.7901 0.9606 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1918 0.3641 2.2579 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5029 -0.1864 -0.0749 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6534 -0.8524 0.3066 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4538 -1.2439 -0.9294 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9129 0.0199 -1.5820 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6468 0.8967 -0.6154 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9903 0.9871 0.7330 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4573 -0.1930 1.1804 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9978 0.5243 -0.5277 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8097 0.7377 -2.0737 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5603 -1.9979 -0.5752 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6900 -2.0825 -1.4983 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8261 -3.3201 -0.9159 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1029 -2.1557 0.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2303 -1.7925 -1.7573 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5845 -1.8761 0.7125 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5958 -0.5819 1.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8963 1.7604 -0.1161 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4809 1.8374 0.9621 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8661 1.5012 -1.3883 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9787 1.3206 -0.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7166 -0.0321 -1.6609 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4228 -1.3429 -1.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7683 -1.7297 -0.5039 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4469 -1.9250 0.6538 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9968 -0.1728 3.1695 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 -1.0525 2.5146 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8955 -2.6204 3.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3702 -1.0050 -0.1485 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9312 -0.0212 2.6424 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5685 -1.3834 1.7156 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2504 0.0512 2.1391 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4231 1.5433 1.7441 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1330 0.9312 -0.3413 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3328 2.0123 0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0851 2.2568 -0.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6551 -1.5589 -0.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2120 0.2464 -2.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2163 -1.2577 -2.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1974 -0.1419 -2.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1772 1.2307 -3.0092 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8815 0.9037 -1.2486 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2994 2.5466 1.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2203 3.1775 -0.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2202 2.1445 -0.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0760 3.1497 0.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7933 0.2539 1.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8471 1.9022 1.2929 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6443 1.3562 3.0594 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2844 2.8909 -0.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6058 -1.2042 -2.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3598 -0.9588 1.7309 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5937 -2.5231 1.4928 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7573 1.1646 2.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3436 -1.8168 0.7709 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8340 -1.8022 -1.6643 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6201 -0.1787 -2.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6465 1.9308 -1.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7976 1.2792 1.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2638 1.8391 0.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4059 0.8054 0.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0120 1.7206 -2.1311 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6559 -2.1284 0.3994 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 1 23 30 1 6 20 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 4 37 1 0 3 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 42 45 1 0 41 46 1 0 40 47 1 0 7 2 1 0 28 9 1 0 36 31 1 0 44 39 1 0 27 12 1 0 24 15 1 0 23 18 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 6 3 52 1 1 4 53 1 1 5 54 1 0 5 55 1 0 6 56 1 6 9 57 1 6 10 58 1 0 10 59 1 0 11 60 1 0 11 61 1 0 13 62 1 0 13 63 1 0 14 64 1 0 15 65 1 0 16 66 1 0 16 67 1 0 17 68 1 0 17 69 1 0 19 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 21 74 1 0 21 75 1 0 22 76 1 0 22 77 1 0 24 78 1 0 25 79 1 0 25 80 1 0 26 81 1 0 26 82 1 0 28 83 1 0 28 84 1 0 29 85 1 0 30 86 1 0 32 87 1 0 36 88 1 0 36 89 1 0 37 90 1 0 39 91 1 1 40 92 1 6 41 93 1 6 42 94 1 6 43 95 1 0 43 96 1 0 45 97 1 0 46 98 1 0 47 99 1 0 M END

Standard InCHIKey	WDAWHSXOXNKHHI-MQDLSUFXSA-N
Standard InCHI	InChI=1S/C34H52O13/c1-17-29(47-30-28(40)27(39)24(37)15-44-30)23(36)12-26(45-17)46-19-3-8-32(16-35)21-4-7-31(2)20(18-11-25(38)43-14-18)6-10-34(31,42)22(21)5-9-33(32,41)13-19/h11,17,19-24,26-30,35-37,39-42H,3-10,12-16H2,1-2H3/t17-,19+,20?,21?,22?,23+,24-,26+,27+,28-,29-,30+,31-,32+,33+,34+/m1/s1
SMILES	C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]1CC[C@]2(CO)C3CC[C@]4(C)C(CC[C@@]4(C3CC[C@@]2(C1)O)O)C1=CC(=O)OC1)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	668.34	Volume:	645.725 ? Van der Waals volume.
Dense:	1.035	LogP:	-0.055 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.619 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.951 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	38.0
TPSA:	204.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.148	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.758	Fsp³:	0.912
MCE-18:	134.492 ? 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:	0.534	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.01 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.126	Promiscuous compounds:	0.318

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.62	MDCK Permeability:	-5.168
Pgp-inhibitor:	0.0	Pgp-substrate:	0.998
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):	0.009
20% Bioavailability (F20%):	0.879	30% Bioavailability (F30%):	0.427
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023	MRP1:	0.95
Plasma Protein Binding (PPB):	60.056%	Volume Distribution (VD):	-0.497
Fu:	36.216% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.596
OATP1B3 inhibitor:	0.086	BCRP inhibitor:	0.0
BSEP inhibitor:	0.033

ADMET: Metabolism

CYP1A2-inhibitor:	0.08	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:	0.983	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.024
HLM stability:	0.007 ? 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):

0.95

Half-life (T1/2):

3.38

ADMET: Toxicity

hERG Blockers:	0.061	hERG Blockers (10um):	0.189
Human Hepatotoxicity (H-HT):	0.904	Drug-induced Liver Injury (DILI):	0.544
AMES Toxicity:	0.902	Rat Oral Acute Toxicity:	0.63
Maximum Recommended Daily Dose:	0.973	Skin Sensitization:	1.0
Carcinogencity:	0.775	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.23
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.989
Hematotoxicity:	0.102	Drug-induced Nephrotoxicity:	0.993
Genotoxicity:	0.853	RPMI-8226 Immunitoxicity:	0.665
A549 Cytotoxicity:	0.977	Hek293 Cytotoxicity:	0.973
BCF:	0.473 ? 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:	3.21 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.816 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.817 ? 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
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	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 NPC289897 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	16634
0.1-0.2	29014
0.2-0.3	3839
0.3-0.4	197
0.4-0.5	74
0.5-0.6	66
0.6-0.7	23
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
0.8675	High Similarity	NPC608063
0.7614	Intermediate Similarity	NPC475556
0.7614	Intermediate Similarity	NPC311706
0.7439	Intermediate Similarity	NPC158344
0.7262	Intermediate Similarity	NPC219085
0.7176	Intermediate Similarity	NPC157376
0.7176	Intermediate Similarity	NPC142066
0.7176	Intermediate Similarity	NPC603972
0.66	Remote Similarity	NPC329675
0.6526	Remote Similarity	NPC125077
0.6316	Remote Similarity	NPC32793
0.6316	Remote Similarity	NPC116075
0.63	Remote Similarity	NPC475590
0.6292	Remote Similarity	NPC84987
0.625	Remote Similarity	NPC474418
0.625	Remote Similarity	NPC264336
0.618	Remote Similarity	NPC99728
0.618	Remote Similarity	NPC87250
0.618	Remote Similarity	NPC244402
0.618	Remote Similarity	NPC50305
0.6139	Remote Similarity	NPC329636
0.6129	Remote Similarity	NPC471354
0.6129	Remote Similarity	NPC27507
0.6064	Remote Similarity	NPC72260
0.6061	Remote Similarity	NPC146857
0.6044	Remote Similarity	NPC17896
0.6044	Remote Similarity	NPC469755
0.6044	Remote Similarity	NPC284406
0.6044	Remote Similarity	NPC197707
0.6044	Remote Similarity	NPC251866
0.6019	Remote Similarity	NPC120390
0.5978	Remote Similarity	NPC604978
0.5918	Remote Similarity	NPC475629
0.5865	Remote Similarity	NPC74259
0.5859	Remote Similarity	NPC55532
0.581	Remote Similarity	NPC194716
0.5714	Remote Similarity	NPC32177
0.5714	Remote Similarity	NPC469756
0.5714	Remote Similarity	NPC275901
0.57	Remote Similarity	NPC208193
0.5699	Remote Similarity	NPC34390
0.5595	Remote Similarity	NPC10232
0.5579	Remote Similarity	NPC180079
0.5556	Remote Similarity	NPC236973
0.5545	Remote Similarity	NPC59288
0.5532	Remote Similarity	NPC6108
0.5532	Remote Similarity	NPC77299
0.5532	Remote Similarity	NPC89514
0.5532	Remote Similarity	NPC480906
0.55	Remote Similarity	NPC188234
0.549	Remote Similarity	NPC469749
0.5474	Remote Similarity	NPC243196
0.5474	Remote Similarity	NPC76572
0.5474	Remote Similarity	NPC193382
0.5437	Remote Similarity	NPC247190
0.5417	Remote Similarity	NPC77319
0.5417	Remote Similarity	NPC471351
0.5417	Remote Similarity	NPC471355
0.5368	Remote Similarity	NPC5311
0.5333	Remote Similarity	NPC475219
0.5319	Remote Similarity	NPC99620
0.5319	Remote Similarity	NPC471633
0.5312	Remote Similarity	NPC10823
0.5312	Remote Similarity	NPC480914
0.5288	Remote Similarity	NPC329986
0.5288	Remote Similarity	NPC140092
0.5243	Remote Similarity	NPC486135
0.5243	Remote Similarity	NPC486137
0.5208	Remote Similarity	NPC469750
0.5204	Remote Similarity	NPC9499
0.5204	Remote Similarity	NPC471360
0.5204	Remote Similarity	NPC469751
0.5204	Remote Similarity	NPC471361
0.5204	Remote Similarity	NPC86159
0.5204	Remote Similarity	NPC469752
0.5204	Remote Similarity	NPC469754
0.5204	Remote Similarity	NPC70542
0.52	Remote Similarity	NPC173555
0.5149	Remote Similarity	NPC30483
0.5149	Remote Similarity	NPC470897
0.5138	Remote Similarity	NPC475419
0.5104	Remote Similarity	NPC309034
0.5102	Remote Similarity	NPC146456
0.51	Remote Similarity	NPC480907
0.5096	Remote Similarity	NPC486143
0.5096	Remote Similarity	NPC486142
0.5096	Remote Similarity	NPC486149
0.5093	Remote Similarity	NPC486136
0.5091	Remote Similarity	NPC117445
0.5091	Remote Similarity	NPC474908
0.5091	Remote Similarity	NPC308262
0.5089	Remote Similarity	NPC474423
0.5051	Remote Similarity	NPC483822
0.5049	Remote Similarity	NPC480910
0.5049	Remote Similarity	NPC480909
0.5048	Remote Similarity	NPC232785
0.5048	Remote Similarity	NPC486139

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC289897 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6379
0.1-0.2	2677
0.2-0.3	80
0.3-0.4	1
0.4-0.5	7
0.5-0.6	4
0.6-0.7	2
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
0.6064	Remote Similarity	NPD8294	Phase 4
0.6044	Remote Similarity	NPD7319	Approved
0.57	Remote Similarity	NPD8377	Phase 4
0.5417	Remote Similarity	NPD8335	Phase 4
0.5361	Remote Similarity	NPD8380	Approved
0.52	Remote Similarity	NPD8296	Phase 4

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