NPASS Compound

Natural Product: NPC479739

Natural Product ID	NPC479739
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IXJOXYJIHGCFCX-VYXVHPRESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 98103 0 0 0 0 0 0 0 0999 V2000 -7.2235 1.0445 -3.2290 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2364 1.3675 -2.4099 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4092 2.6025 -1.6166 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0111 2.3756 -0.2140 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6921 0.9377 0.1521 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2762 0.9500 1.5782 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0791 0.1512 1.9485 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9476 0.3439 1.0220 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3914 1.7366 1.2140 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3503 0.2404 -0.4263 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3638 0.1325 -1.2854 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9128 0.1031 -0.9578 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6509 -0.1347 0.4733 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6557 -0.8670 0.7634 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7353 -2.2261 0.1858 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7400 -0.0141 0.1317 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1157 -0.4503 0.5726 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1831 -0.2344 2.0598 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1699 -1.1161 2.7623 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5209 -2.5656 2.7280 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2437 -0.6649 4.2162 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9076 0.6916 4.3212 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7950 -0.7928 2.2697 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2825 -1.5762 2.9477 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6004 -0.8320 2.6759 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8396 -0.7041 1.1923 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3061 -2.0250 0.6816 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4611 -0.4096 2.5552 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0867 0.3870 -0.0235 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1479 -0.0759 -0.7898 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2240 -1.3224 -0.9463 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1351 0.8218 -1.3923 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1085 0.2981 -2.1081 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1455 1.0886 -2.7540 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1063 0.4156 -3.4805 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1435 1.0565 -4.1397 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2023 2.4140 -4.0562 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2486 3.0962 -3.3338 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2238 2.4518 -2.6836 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1950 3.1601 -4.6751 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7823 0.2443 -0.8001 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9790 0.5901 -2.2502 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1456 -0.6744 -3.1014 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0280 0.2236 0.1118 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1029 0.7715 -0.1396 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0023 -1.1380 0.3804 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1251 1.6253 -3.3414 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1435 0.1586 -3.8302 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4089 3.0697 -1.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7011 3.3576 -2.0698 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8532 2.6632 0.4837 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1153 2.9851 0.0586 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1149 0.5665 2.2399 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1486 2.0049 1.9722 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7372 0.5497 2.9544 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3887 -0.8782 2.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2584 2.4334 1.4135 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9161 2.1547 0.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7785 1.8259 2.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6291 0.0537 -2.3485 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4539 -0.6412 -1.6434 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4848 1.0773 -1.2679 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4652 0.8749 0.9551 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7103 -2.4489 -0.3450 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0084 -2.4166 -0.6443 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6222 -3.0591 0.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7068 -0.0249 -0.9571 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6201 1.0430 0.4680 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3383 -1.4905 0.3601 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 0.8171 2.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6530 -3.1431 3.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 -2.9176 1.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3332 -2.7266 3.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2947 -0.7450 4.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5849 -1.2231 4.8914 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5705 1.2169 4.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6148 0.2858 2.5273 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1525 -1.5920 4.0282 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3452 -2.6350 2.6266 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5242 0.1131 3.2114 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4054 -1.4460 3.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3607 -2.1413 -0.3995 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3638 -2.2022 1.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7493 -2.8759 1.1769 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6004 0.2161 3.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0597 1.8694 -1.2493 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1156 -0.7798 -2.2061 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1012 -0.6691 -3.5764 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8869 0.4910 -4.7058 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2899 4.1915 -3.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4866 2.9950 -2.1242 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1159 3.3004 -4.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0763 -0.8608 -0.7440 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1652 1.2260 -2.6716 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0993 -1.1900 -2.8112 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2219 -0.3822 -4.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3617 -1.4304 -2.8986 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8250 -1.5549 0.8428 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 18 28 1 0 17 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 10 41 1 0 41 42 1 0 42 43 1 0 5 44 1 1 44 45 2 0 44 46 1 0 42 2 1 0 41 5 1 0 26 8 1 0 39 34 1 0 26 13 1 0 23 14 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 6 53 1 0 6 54 1 0 7 55 1 0 7 56 1 0 9 57 1 0 9 58 1 0 9 59 1 0 11 60 1 0 12 61 1 0 12 62 1 0 13 63 1 1 15 64 1 0 15 65 1 0 15 66 1 0 16 67 1 0 16 68 1 0 17 69 1 1 18 70 1 6 20 71 1 0 20 72 1 0 20 73 1 0 21 74 1 0 21 75 1 0 22 76 1 0 23 77 1 1 24 78 1 0 24 79 1 0 25 80 1 0 25 81 1 0 27 82 1 0 27 83 1 0 27 84 1 0 28 85 1 0 32 86 1 0 33 87 1 0 35 88 1 0 36 89 1 0 38 90 1 0 39 91 1 0 40 92 1 0 41 93 1 6 42 94 1 6 43 95 1 0 43 96 1 0 43 97 1 0 46 98 1 0 M END

Standard InCHIKey	IXJOXYJIHGCFCX-VYXVHPRESA-N
Standard InCHI	InChI=1S/C39H52O7/c1-23-15-18-39(34(44)45)20-19-37(5)27(32(39)24(23)2)12-13-30-35(3)21-28(46-31(42)14-9-25-7-10-26(41)11-8-25)33(43)36(4,22-40)29(35)16-17-38(30,37)6/h7-12,14,24,28-30,32-33,40-41,43H,1,13,15-22H2,2-6H3,(H,44,45)/b14-9+/t24-,28+,29+,30+,32-,33-,35-,36-,37+,38+,39-/m0/s1
SMILES	C=C1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O)OC(=O)/C=C/c3ccc(cc3)O)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	632.37	Volume:	672.201 ? Van der Waals volume.
Dense:	0.941	LogP:	3.65 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.262 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.039 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	36.0
TPSA:	124.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.158	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.343	Fsp³:	0.641
MCE-18:	161.719 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.983	Fluc inhibitor:	0.976 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.106 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.032 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.112	Promiscuous compounds:	0.081

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.745	MDCK Permeability:	-5.192
Pgp-inhibitor:	0.059	Pgp-substrate:	0.004
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%):	0.998	30% Bioavailability (F30%):	0.942
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047	MRP1:	0.623
Plasma Protein Binding (PPB):	85.696%	Volume Distribution (VD):	-0.146
Fu:	9.995% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.846	BCRP inhibitor:	0.102
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.948
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.0 ? 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):

2.357

Half-life (T1/2):

1.408

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.038
Human Hepatotoxicity (H-HT):	0.705	Drug-induced Liver Injury (DILI):	0.753
AMES Toxicity:	0.357	Rat Oral Acute Toxicity:	0.225
Maximum Recommended Daily Dose:	0.365	Skin Sensitization:	0.992
Carcinogencity:	0.71	Eye Corrosion:	0.001
Eye Irritation:	0.299	Respiratory Toxicity:	0.512
Drug-induced Neurotoxicity:	0.107	Ototoxicity:	0.765
Hematotoxicity:	0.411	Drug-induced Nephrotoxicity:	0.952
Genotoxicity:	0.662	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.344	Hek293 Cytotoxicity:	0.377
BCF:	0.633 ? 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:	3.867 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.565 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.874 ? 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
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	root	n.a.	PMID[18481026]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	root	n.a.	PMID[19336935]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32315181]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26333	Actinidia arguta	Species	Actinidiaceae	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
Inhibition	1

Activity Type	# Activity
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
NPT2	Others	Unspecified	n.a.	Inhibition	=	70.1	%	PMID[32315181]

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 NPC479739 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	7342
0.1-0.2	36608
0.2-0.3	5228
0.3-0.4	519
0.4-0.5	109
0.5-0.6	35
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8427	Intermediate Similarity	NPC479744
0.7957	Intermediate Similarity	NPC324798
0.7957	Intermediate Similarity	NPC479742
0.7245	Intermediate Similarity	NPC479740
0.7245	Intermediate Similarity	NPC479741
0.6768	Remote Similarity	NPC178093
0.6667	Remote Similarity	NPC304110
0.6667	Remote Similarity	NPC27518
0.6667	Remote Similarity	NPC611516
0.6566	Remote Similarity	NPC172311
0.65	Remote Similarity	NPC132126
0.6364	Remote Similarity	NPC22676
0.6238	Remote Similarity	NPC482052
0.6238	Remote Similarity	NPC605663
0.6176	Remote Similarity	NPC25491
0.6154	Remote Similarity	NPC479745
0.5962	Remote Similarity	NPC475482
0.5962	Remote Similarity	NPC479747
0.5962	Remote Similarity	NPC479746
0.5889	Remote Similarity	NPC127689
0.5824	Remote Similarity	NPC20235
0.5824	Remote Similarity	NPC299996
0.5784	Remote Similarity	NPC486700
0.5784	Remote Similarity	NPC275312
0.578	Remote Similarity	NPC118033
0.5686	Remote Similarity	NPC477874
0.5673	Remote Similarity	NPC198621
0.5673	Remote Similarity	NPC216940
0.5619	Remote Similarity	NPC54627
0.5619	Remote Similarity	NPC249817
0.5607	Remote Similarity	NPC482051
0.5545	Remote Similarity	NPC485587
0.5514	Remote Similarity	NPC482049
0.5514	Remote Similarity	NPC482050
0.549	Remote Similarity	NPC173569
0.5405	Remote Similarity	NPC601567
0.5405	Remote Similarity	NPC606631
0.5376	Remote Similarity	NPC25299
0.5376	Remote Similarity	NPC481322
0.5357	Remote Similarity	NPC481234
0.5357	Remote Similarity	NPC479431
0.5333	Remote Similarity	NPC171007
0.5333	Remote Similarity	NPC190849
0.5321	Remote Similarity	NPC610795
0.5283	Remote Similarity	NPC488215
0.5263	Remote Similarity	NPC481235
0.5234	Remote Similarity	NPC487491
0.5234	Remote Similarity	NPC262970
0.5229	Remote Similarity	NPC487490
0.5185	Remote Similarity	NPC488214
0.514	Remote Similarity	NPC477873

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479739 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3643
0.1-0.2	5418
0.2-0.3	85
0.3-0.4	3
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