NPASS Compound

Natural Product: NPC488468

Natural Product ID	NPC488468
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZQGQHCBDBUULPU-ZHEVSQDMSA-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] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid 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 104109 0 0 0 0 0 0 0 0999 V2000 4.4143 3.1722 2.3851 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8543 3.0122 0.9667 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1679 3.6972 0.6560 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6610 2.9069 -0.5386 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3202 1.4950 -0.1575 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3378 0.5734 -1.3136 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2447 0.3679 -2.0030 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1003 1.0551 -1.5856 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8248 1.0918 -0.1763 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0335 1.5669 0.5784 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5105 -0.1689 0.2572 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1946 -0.2849 0.7599 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4967 -1.2513 -0.1465 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2395 -2.5731 -0.0190 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4748 -2.9782 1.3907 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7144 -1.8878 2.3715 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1693 -1.8911 2.8705 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3090 -1.1192 4.0006 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2789 -0.6437 2.0579 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4646 -3.8798 1.8043 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4825 -2.4304 -0.6479 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1614 -1.3522 -0.0240 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6391 -1.0585 -1.0665 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4724 0.1697 -0.7440 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9279 -0.1488 -0.5843 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2950 -0.9081 0.6056 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0996 -1.9542 0.5422 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6436 -2.3852 -0.6847 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7258 -1.3765 -1.6758 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3542 -0.8193 -1.8763 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3676 -1.7578 -2.4472 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9416 -3.0161 -3.0378 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4230 -2.1084 -1.5194 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5267 -0.3568 -1.1676 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6778 -0.1409 -1.9384 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8970 -0.5335 -1.1774 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7256 0.6217 -0.6640 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7166 1.7450 -0.4307 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2140 2.1233 -1.8048 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2923 3.3086 -1.6542 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1157 2.9801 -0.9742 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6600 1.0870 -2.4993 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3395 2.8169 0.1605 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3499 0.2433 0.5267 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7177 -1.4321 -1.8863 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7865 -0.5253 1.9096 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0172 0.4455 2.1313 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1250 -1.2348 3.0760 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6529 -0.8944 4.3545 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5705 -0.1194 -1.7032 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5801 -0.8997 -2.6859 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7662 0.0458 -1.0228 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9495 -0.6444 -1.4282 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0605 3.6728 1.7006 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2969 3.3109 2.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6342 2.2493 2.9586 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8897 4.0374 2.8897 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0858 3.4964 0.2988 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0012 4.7681 0.3797 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7737 3.0062 -0.6492 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1347 3.2123 -1.4658 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1465 1.1538 0.5296 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2634 -0.3085 -2.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9920 1.8086 -0.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1463 0.9800 1.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7512 0.7154 0.6702 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7119 -0.9085 -1.1826 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7100 -3.3866 -0.5525 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4026 -3.6278 1.3893 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1409 -2.1897 3.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7902 -1.5876 2.0216 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4458 -2.9494 3.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2924 -1.0108 4.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1607 -3.6658 2.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9975 -3.2677 -0.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0112 -0.7562 -1.9286 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4173 0.9184 -1.5875 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9916 0.6753 0.1020 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4831 0.8124 -0.5401 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3802 -2.5290 1.4181 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1631 -1.8207 -2.5971 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4860 0.0195 -2.6109 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8217 -1.2501 -3.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1783 -3.7824 -2.2719 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7996 -2.8364 -3.7166 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1444 -3.4638 -3.6689 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6025 -0.8885 -2.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5790 -1.1062 -0.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4536 0.9637 -1.4292 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8737 1.3502 0.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1004 2.4763 -2.3725 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9816 3.7240 -2.6406 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7638 4.1397 -1.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4537 3.7008 -1.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0469 2.5425 0.8214 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4183 -0.7449 0.5586 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3519 -1.4939 -2.8032 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6021 -1.2398 4.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2546 -1.5211 5.0764 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8231 0.1446 4.6475 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1580 -1.4847 -0.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8092 -1.0917 -2.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8361 -0.0118 -1.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9334 3.2945 1.4915 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 2 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 15 20 1 0 14 21 1 0 13 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 26 46 1 0 46 47 2 0 46 48 1 0 48 49 1 0 6 50 1 0 50 51 2 0 50 52 1 0 52 53 1 0 3 54 1 0 10 2 1 0 19 12 1 0 33 23 1 0 42 35 1 0 10 5 1 0 30 25 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 0 4 61 1 0 5 62 1 1 7 63 1 0 9 64 1 6 10 65 1 1 12 66 1 1 13 67 1 6 14 68 1 6 15 69 1 6 16 70 1 1 17 71 1 0 17 72 1 0 18 73 1 0 20 74 1 0 21 75 1 0 23 76 1 6 24 77 1 0 24 78 1 0 25 79 1 1 27 80 1 0 29 81 1 6 30 82 1 6 31 83 1 6 32 84 1 0 32 85 1 0 32 86 1 0 35 87 1 6 36 88 1 1 37 89 1 6 38 90 1 1 39 91 1 6 40 92 1 0 40 93 1 0 41 94 1 0 43 95 1 0 44 96 1 0 45 97 1 0 49 98 1 0 49 99 1 0 49100 1 0 53101 1 0 53102 1 0 53103 1 0 54104 1 0 M END

Standard InCHIKey	ZQGQHCBDBUULPU-ZHEVSQDMSA-N
Standard InCHI	InChI=1S/C34H50O20/c1-11-17(37)5-13-15(29(43)45-3)9-47-31(21(11)13)54-34-28(26(41)24(39)19(8-36)51-34)52-20-6-14-16(30(44)46-4)10-48-32(22(14)12(2)49-20)53-33-27(42)25(40)23(38)18(7-35)50-33/h9-14,17-28,31-42H,5-8H2,1-4H3/t11-,12-,13+,14+,17-,18+,19+,20+,21+,22+,23+,24+,25-,26-,27+,28+,31-,32-,33-,34-/m0/s1
SMILES	C[C@H]1[C@H](C[C@@H]2C(=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@@H]1C[C@@H]2C(=CO[C@H]([C@@H]2[C@H](C)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC)C(=O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	778.29	Volume:	710.54 ? Van der Waals volume.
Dense:	1.095	LogP:	-1.159 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.401 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.01 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	35.0
TPSA:	288.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.1	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.024	Fsp³:	0.824
MCE-18:	113.806 ? 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:	0.433	Fluc inhibitor:	0.266 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.114 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.447	Promiscuous compounds:	0.148

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.892	MDCK Permeability:	-5.421
Pgp-inhibitor:	0.0	Pgp-substrate:	0.413
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):	0.903
20% Bioavailability (F20%):	0.34	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.946
Plasma Protein Binding (PPB):	46.347%	Volume Distribution (VD):	-0.502
Fu:	51.888% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
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:	0.264
HLM stability:	0.031 ? 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):

0.682

Half-life (T1/2):

3.73

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.015
Human Hepatotoxicity (H-HT):	0.735	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.989	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.011	Skin Sensitization:	1.0
Carcinogencity:	0.119	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	1.0
Hematotoxicity:	0.951	Drug-induced Nephrotoxicity:	0.987
Genotoxicity:	0.363	RPMI-8226 Immunitoxicity:	0.223
A549 Cytotoxicity:	0.934	Hek293 Cytotoxicity:	0.402
BCF:	0.282 ? 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:	2.664 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.542 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.565 ? 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
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[29140705]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12588	Cornus officinalis	Species	Cornaceae	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
IC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT38	Individual protein	Signal transducer and activator of transcription 3	Homo sapiens	IC50	=	40500.0	nM	PMID[29140705]

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 NPC488468 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	21293
0.1-0.2	25204
0.2-0.3	3071
0.3-0.4	213
0.4-0.5	40
0.5-0.6	14
0.6-0.7	12
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8493	Intermediate Similarity	NPC488457
0.8493	Intermediate Similarity	NPC488464
0.8493	Intermediate Similarity	NPC488463
0.7949	Intermediate Similarity	NPC488467
0.7195	Intermediate Similarity	NPC488469
0.7183	Intermediate Similarity	NPC35185
0.7183	Intermediate Similarity	NPC4899
0.7183	Intermediate Similarity	NPC177013
0.7123	Intermediate Similarity	NPC470573
0.7123	Intermediate Similarity	NPC120021
0.7123	Intermediate Similarity	NPC216826
0.6962	Remote Similarity	NPC488470
0.6933	Remote Similarity	NPC488472
0.6933	Remote Similarity	NPC257424
0.6625	Remote Similarity	NPC488456
0.6625	Remote Similarity	NPC488471
0.6625	Remote Similarity	NPC488466
0.6625	Remote Similarity	NPC488465
0.6625	Remote Similarity	NPC488460
0.6625	Remote Similarity	NPC488462
0.6133	Remote Similarity	NPC474730
0.6118	Remote Similarity	NPC488461
0.6118	Remote Similarity	NPC488458
0.5952	Remote Similarity	NPC488459
0.5823	Remote Similarity	NPC231710
0.5823	Remote Similarity	NPC270908
0.5823	Remote Similarity	NPC65665
0.5696	Remote Similarity	NPC27687
0.5443	Remote Similarity	NPC475928
0.5316	Remote Similarity	NPC170432
0.5309	Remote Similarity	NPC106668
0.5309	Remote Similarity	NPC37240
0.5238	Remote Similarity	NPC41681
0.5125	Remote Similarity	NPC117596
0.5062	Remote Similarity	NPC255677
0.5062	Remote Similarity	NPC22149
0.5062	Remote Similarity	NPC306344

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488468 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7283
0.1-0.2	1816
0.2-0.3	51
0.3-0.4	0
0.4-0.5	0
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