NPASS Compound

Natural Product: NPC87386

Natural Product ID	NPC87386
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YFERBGPVRSLDSL-GVZNLTFMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11274280
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 91 96 0 0 0 0 0 0 0 0999 V2000 -5.6892 0.1130 -3.1939 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3252 -0.4880 -3.0729 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3732 0.0791 -4.1341 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2476 -0.9282 -4.2330 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7725 -1.2194 -2.8343 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3979 -0.3724 -1.7818 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7897 -0.4170 -1.8153 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9560 -0.8281 -0.5164 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7989 0.0091 0.5934 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6330 0.7865 0.6212 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2267 0.7314 -0.2996 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4653 1.6187 1.7027 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6748 2.4250 1.7958 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8217 3.2516 2.8850 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1330 3.2995 3.8856 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2465 2.5121 3.7959 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4235 1.6588 2.6957 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4751 0.9065 2.5985 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7291 0.0636 1.5897 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9596 -0.7169 1.6437 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9121 -0.3404 2.5962 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0856 -1.0154 2.8010 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3823 -2.1332 2.0472 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4601 -2.5140 1.1117 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2529 -1.8190 0.9021 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6622 -3.6354 0.2911 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5468 -2.8622 2.1994 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0060 4.1326 4.9917 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5925 2.3284 0.7584 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3942 -1.0404 -2.8339 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2780 -2.2106 -2.4794 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0059 -2.8173 -3.6476 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4712 -2.5641 -3.6871 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1788 -2.6328 -2.3624 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1422 -2.8443 -1.2830 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7531 -2.7010 0.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1924 -1.3928 0.3453 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7757 -0.9380 1.5095 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9267 -1.7715 2.4366 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2080 0.4561 1.6793 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7426 0.8173 2.8069 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2213 2.1366 3.1471 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7435 2.4273 4.3851 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1951 3.6865 4.7113 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1345 4.7019 3.7911 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6176 4.4448 2.5421 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1645 3.1541 2.2355 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5615 5.4711 1.6277 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5997 5.9826 4.1407 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0494 -2.0068 -1.3825 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0129 -3.7690 -2.3176 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6978 -1.2717 -4.2221 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7048 -4.1931 -3.7962 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2574 -0.3693 -5.0312 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0766 0.1532 -5.3215 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6800 1.1409 -3.6287 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2307 0.1624 -2.2248 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3353 -0.4960 -3.8845 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4135 -1.5707 -3.3276 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9555 1.0577 -3.8214 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6953 -1.8518 -4.6790 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0266 -2.2792 -2.5741 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0825 0.7069 -1.8467 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7048 3.8684 2.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0453 2.4772 4.5222 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7398 0.5346 3.2253 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8120 -0.7147 3.5399 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5670 -2.1717 0.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0060 -4.3888 0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9907 -2.8288 3.1235 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6525 4.8828 5.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4098 2.9201 0.8356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5303 -2.9615 -2.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5766 -2.3510 -4.5747 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9553 -3.2417 -4.4440 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7793 -1.7116 -2.1788 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7833 -3.8890 -1.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9905 -3.0675 0.8099 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6380 -3.3732 0.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0880 1.1632 0.8957 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8413 0.0422 3.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8185 1.6596 5.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6080 3.9295 5.6824 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7719 3.0197 1.2320 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2962 6.0737 1.3433 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5882 6.1966 4.1399 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9443 -3.5535 -2.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1543 -1.1434 -5.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1273 -4.3409 -3.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6697 -0.1702 -5.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6413 0.7345 -6.0055 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 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 23 27 1 0 15 28 1 0 13 29 1 0 5 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 2 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 45 49 1 0 35 50 1 0 34 51 1 0 33 52 1 0 32 53 1 0 4 54 1 0 3 55 1 0 7 2 1 0 19 9 2 0 25 20 1 0 50 31 1 0 17 12 1 0 47 42 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 6 3 60 1 1 4 61 1 6 5 62 1 1 6 63 1 6 14 64 1 0 16 65 1 0 21 66 1 0 22 67 1 0 25 68 1 0 26 69 1 0 27 70 1 0 28 71 1 0 29 72 1 0 31 73 1 1 32 74 1 6 33 75 1 6 34 76 1 1 35 77 1 1 36 78 1 0 36 79 1 0 40 80 1 0 41 81 1 0 43 82 1 0 44 83 1 0 47 84 1 0 48 85 1 0 49 86 1 0 51 87 1 0 52 88 1 0 53 89 1 0 54 90 1 0 55 91 1 0 M END

Standard InCHIKey	YFERBGPVRSLDSL-GVZNLTFMSA-N
Standard InCHI	InChI=1S/C36H36O19/c1-13-26(44)30(48)34(55-35-31(49)29(47)27(45)23(53-35)12-50-24(43)7-3-14-2-5-17(38)19(40)8-14)36(51-13)54-33-28(46)25-21(42)10-16(37)11-22(25)52-32(33)15-4-6-18(39)20(41)9-15/h2-11,13,23,26-27,29-31,34-42,44-45,47-49H,12H2,1H3/b7-3+/t13-,23+,26-,27+,29-,30+,31+,34+,35-,36-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)O)O)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	772.19	Volume:	712.614 ? Van der Waals volume.
Dense:	1.084	LogP:	1.327 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.424 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.599 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	38.0
TPSA:	315.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.061	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.126	Fsp³:	0.333
MCE-18:	143.5 ? 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:	1
Colloidal aggregators:	0.714	Fluc inhibitor:	0.504 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.907 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.259	Promiscuous compounds:	0.635

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.4	MDCK Permeability:	-5.001
Pgp-inhibitor:	0.0	Pgp-substrate:	0.024
PAMPA:	0.991 ? 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):	0.619
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.005
Plasma Protein Binding (PPB):	85.189%	Volume Distribution (VD):	-0.139
Fu:	11.127% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.177
BSEP inhibitor:	0.011

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:	0.986
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.019
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.863 ? 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):

2.2

Half-life (T1/2):

5.263

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.385
Human Hepatotoxicity (H-HT):	0.247	Drug-induced Liver Injury (DILI):	0.951
AMES Toxicity:	0.924	Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.317	Skin Sensitization:	1.0
Carcinogencity:	0.05	Eye Corrosion:	0.0
Eye Irritation:	0.33	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.987
Hematotoxicity:	0.009	Drug-induced Nephrotoxicity:	0.038
Genotoxicity:	0.98	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.993	Hek293 Cytotoxicity:	0.854
BCF:	0.707 ? 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:	3.56 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.88 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.462 ? 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
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15577228]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	calyx	n.a.	PMID[21561086]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085682]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24086493]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37324556]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	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 NPC87386 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	16665
0.1-0.2	28946
0.2-0.3	3359
0.3-0.4	504
0.4-0.5	183
0.5-0.6	126
0.6-0.7	43
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	Natural Product ID
0.7921	Intermediate Similarity	NPC81042
0.7909	Intermediate Similarity	NPC21359
0.7909	Intermediate Similarity	NPC460984
0.7523	Intermediate Similarity	NPC488740
0.7523	Intermediate Similarity	NPC488736
0.7523	Intermediate Similarity	NPC488733
0.7404	Intermediate Similarity	NPC214621
0.7404	Intermediate Similarity	NPC34267
0.7387	Intermediate Similarity	NPC488737
0.7364	Intermediate Similarity	NPC162394
0.7345	Intermediate Similarity	NPC25946
0.7308	Intermediate Similarity	NPC223426
0.7304	Intermediate Similarity	NPC473554
0.7265	Intermediate Similarity	NPC487502
0.7143	Intermediate Similarity	NPC95866
0.7087	Intermediate Similarity	NPC122467
0.7027	Intermediate Similarity	NPC488734
0.7027	Intermediate Similarity	NPC488735
0.7027	Intermediate Similarity	NPC488739
0.7027	Intermediate Similarity	NPC488732
0.7027	Intermediate Similarity	NPC488738
0.7	Intermediate Similarity	NPC139571
0.6967	Remote Similarity	NPC487501
0.6822	Remote Similarity	NPC218161
0.6792	Remote Similarity	NPC85751
0.6792	Remote Similarity	NPC19240
0.6748	Remote Similarity	NPC487500
0.6667	Remote Similarity	NPC97817
0.6639	Remote Similarity	NPC249560
0.6636	Remote Similarity	NPC89127
0.6612	Remote Similarity	NPC30011
0.6552	Remote Similarity	NPC480444
0.6538	Remote Similarity	NPC155877
0.6535	Remote Similarity	NPC476215
0.6509	Remote Similarity	NPC12013
0.6509	Remote Similarity	NPC11432
0.6509	Remote Similarity	NPC477613
0.6429	Remote Similarity	NPC477895
0.6372	Remote Similarity	NPC217520
0.6372	Remote Similarity	NPC303694
0.6356	Remote Similarity	NPC241781
0.6341	Remote Similarity	NPC72554
0.633	Remote Similarity	NPC471669
0.6325	Remote Similarity	NPC156785
0.6321	Remote Similarity	NPC35167
0.6311	Remote Similarity	NPC254855
0.6311	Remote Similarity	NPC116864
0.6311	Remote Similarity	NPC244776
0.6311	Remote Similarity	NPC94610
0.6311	Remote Similarity	NPC275977
0.625	Remote Similarity	NPC89052
0.6226	Remote Similarity	NPC203259
0.6226	Remote Similarity	NPC33054
0.6226	Remote Similarity	NPC176740
0.6226	Remote Similarity	NPC471725
0.6226	Remote Similarity	NPC134532
0.6226	Remote Similarity	NPC602582
0.6216	Remote Similarity	NPC602448
0.6179	Remote Similarity	NPC231787
0.6126	Remote Similarity	NPC221342
0.6126	Remote Similarity	NPC476470
0.6102	Remote Similarity	NPC480445
0.6098	Remote Similarity	NPC487499
0.6019	Remote Similarity	NPC255157
0.6019	Remote Similarity	NPC259896
0.5981	Remote Similarity	NPC163242
0.5981	Remote Similarity	NPC272068
0.5862	Remote Similarity	NPC173837
0.5833	Remote Similarity	NPC67326
0.5825	Remote Similarity	NPC216496
0.5804	Remote Similarity	NPC221288
0.5804	Remote Similarity	NPC97119
0.5804	Remote Similarity	NPC194836
0.5804	Remote Similarity	NPC91493
0.5804	Remote Similarity	NPC605081
0.578	Remote Similarity	NPC156869
0.5755	Remote Similarity	NPC170052
0.5755	Remote Similarity	NPC135846
0.5752	Remote Similarity	NPC220173
0.5752	Remote Similarity	NPC477629
0.5746	Remote Similarity	NPC33083
0.5741	Remote Similarity	NPC258044
0.5741	Remote Similarity	NPC217387
0.5739	Remote Similarity	NPC96605
0.5739	Remote Similarity	NPC280642
0.5714	Remote Similarity	NPC37668
0.5714	Remote Similarity	NPC470718
0.5714	Remote Similarity	NPC473327
0.5702	Remote Similarity	NPC292929
0.5702	Remote Similarity	NPC36138
0.5688	Remote Similarity	NPC173582
0.5688	Remote Similarity	NPC265885
0.5688	Remote Similarity	NPC181465
0.5688	Remote Similarity	NPC215710
0.5688	Remote Similarity	NPC473438
0.5688	Remote Similarity	NPC253788
0.5686	Remote Similarity	NPC127546
0.5686	Remote Similarity	NPC57625
0.5686	Remote Similarity	NPC173637
0.5686	Remote Similarity	NPC317489
0.5686	Remote Similarity	NPC223424
0.5686	Remote Similarity	NPC600591
0.5678	Remote Similarity	NPC470712
0.5664	Remote Similarity	NPC101399
0.5664	Remote Similarity	NPC217822
0.5664	Remote Similarity	NPC11847
0.5664	Remote Similarity	NPC198938
0.5656	Remote Similarity	NPC474522
0.5603	Remote Similarity	NPC478277
0.5603	Remote Similarity	NPC483765
0.5603	Remote Similarity	NPC478276
0.5603	Remote Similarity	NPC478275
0.5603	Remote Similarity	NPC92815
0.5603	Remote Similarity	NPC603856
0.5593	Remote Similarity	NPC292019
0.5593	Remote Similarity	NPC202908
0.5581	Remote Similarity	NPC223860
0.5565	Remote Similarity	NPC260504
0.5565	Remote Similarity	NPC89809
0.5545	Remote Similarity	NPC470405
0.5545	Remote Similarity	NPC39834
0.5536	Remote Similarity	NPC253521
0.5536	Remote Similarity	NPC470125
0.5536	Remote Similarity	NPC153755
0.5536	Remote Similarity	NPC113836
0.552	Remote Similarity	NPC192539
0.5517	Remote Similarity	NPC483767
0.5517	Remote Similarity	NPC483769
0.5517	Remote Similarity	NPC483768
0.5517	Remote Similarity	NPC483766
0.5508	Remote Similarity	NPC470416
0.5495	Remote Similarity	NPC304741
0.5495	Remote Similarity	NPC605592
0.5478	Remote Similarity	NPC476472
0.5478	Remote Similarity	NPC294815
0.5478	Remote Similarity	NPC16194
0.5472	Remote Similarity	NPC175107
0.5447	Remote Similarity	NPC470713
0.5446	Remote Similarity	NPC144097
0.5441	Remote Similarity	NPC482521
0.5439	Remote Similarity	NPC104883
0.5439	Remote Similarity	NPC488679
0.5417	Remote Similarity	NPC480441
0.5398	Remote Similarity	NPC154741
0.5391	Remote Similarity	NPC142142
0.5391	Remote Similarity	NPC603079
0.5366	Remote Similarity	NPC474093
0.5366	Remote Similarity	NPC104910
0.536	Remote Similarity	NPC488078
0.5354	Remote Similarity	NPC480442
0.5315	Remote Similarity	NPC471079
0.531	Remote Similarity	NPC129264
0.5304	Remote Similarity	NPC270448
0.5299	Remote Similarity	NPC470445
0.5294	Remote Similarity	NPC599948
0.5268	Remote Similarity	NPC471748
0.5263	Remote Similarity	NPC126784
0.5263	Remote Similarity	NPC241423
0.5217	Remote Similarity	NPC482520
0.5217	Remote Similarity	NPC482519
0.5214	Remote Similarity	NPC76831
0.5207	Remote Similarity	NPC219043
0.5197	Remote Similarity	NPC209550
0.5189	Remote Similarity	NPC145038
0.5189	Remote Similarity	NPC56077
0.5189	Remote Similarity	NPC281131
0.5189	Remote Similarity	NPC253662
0.5189	Remote Similarity	NPC179950
0.5189	Remote Similarity	NPC88789
0.5189	Remote Similarity	NPC491374
0.5185	Remote Similarity	NPC219904
0.5179	Remote Similarity	NPC29958
0.5179	Remote Similarity	NPC609888
0.5143	Remote Similarity	NPC111929
0.5143	Remote Similarity	NPC320283
0.5143	Remote Similarity	NPC41121
0.5138	Remote Similarity	NPC224530
0.513	Remote Similarity	NPC61904
0.5124	Remote Similarity	NPC189564
0.5116	Remote Similarity	NPC480472
0.5096	Remote Similarity	NPC276222
0.5096	Remote Similarity	NPC274618
0.5096	Remote Similarity	NPC118284
0.5096	Remote Similarity	NPC608147
0.5085	Remote Similarity	NPC473071
0.5082	Remote Similarity	NPC48984
0.5048	Remote Similarity	NPC67037
0.5048	Remote Similarity	NPC255615
0.5043	Remote Similarity	NPC470444
0.5041	Remote Similarity	NPC25523
0.5041	Remote Similarity	NPC203145

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87386 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4593
0.1-0.2	4507
0.2-0.3	40
0.3-0.4	7
0.4-0.5	2
0.5-0.6	0
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
0.6226	Remote Similarity	NPD6797	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