NPASS Compound

Natural Product: NPC479744

Natural Product ID	NPC479744
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	STMRENAXEMBDSK-KJVBOBAHSA-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 100105 0 0 0 0 0 0 0 0999 V2000 -5.8903 4.3218 -0.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7879 2.9289 -0.8376 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8552 2.0003 -0.2419 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7561 0.7093 -0.9834 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3785 0.0463 -0.8300 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3008 -0.7567 0.4196 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0750 -0.6568 1.2250 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8100 -0.3055 0.5566 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0762 0.7193 1.4374 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9838 0.3765 -0.7608 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0144 0.3865 -1.6434 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6848 -0.2274 -1.5000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5565 -0.8830 -0.1744 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6498 -1.7911 -0.0359 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6960 -2.9360 -0.9599 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8463 -0.8671 -0.3109 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1596 -1.5126 -0.0588 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2308 -2.4675 1.0685 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0371 -2.6284 1.9140 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8749 -4.1087 2.2831 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3002 -1.9760 3.2906 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5634 -0.6296 3.0352 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7549 -2.1143 1.4309 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4383 -2.9865 1.7698 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7401 -2.2486 1.5756 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8442 -1.4592 0.3257 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3824 -2.3992 -0.7512 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6845 -3.7054 0.5648 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0955 -0.4325 0.1134 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0996 -0.1367 -0.7623 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2150 -0.8550 -1.7875 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0446 0.9728 -0.5649 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0039 1.2362 -1.4246 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9763 2.3090 -1.3058 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9997 3.1786 -0.2678 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9809 4.1651 -0.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9199 4.2960 -1.2593 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8942 3.4085 -2.3163 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9247 2.4285 -2.3257 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8912 5.3128 -1.2074 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2807 1.0335 -1.0275 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4607 2.3469 -0.3250 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3710 3.2788 -0.7923 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3159 -0.9035 -1.9904 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4369 -0.8257 -2.8670 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2586 -1.9176 -2.1199 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8825 4.5196 0.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6386 5.0538 -1.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1325 4.5020 0.5465 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8418 2.9119 -1.9324 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5659 1.8104 0.8207 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8608 2.3939 -0.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4793 -0.0040 -0.4971 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0192 0.8188 -2.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5428 -1.8425 0.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1925 -0.4535 1.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9405 -1.6402 1.7693 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2809 0.0500 2.0872 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4383 0.2346 2.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5916 1.5016 0.8565 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8563 1.2548 2.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2201 0.9112 -2.5921 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0573 0.6246 -1.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4827 -0.8394 -2.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3065 -0.0420 0.5476 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4744 -3.9278 -0.5445 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7457 -3.0226 -1.3699 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0895 -2.7081 -1.8695 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6668 0.0297 0.3340 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7747 -0.5465 -1.3633 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4761 -1.9887 -1.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1026 -2.1540 1.7227 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4044 -4.7081 1.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4195 -4.2291 3.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9321 -4.4836 2.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4094 -2.0304 3.9208 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1892 -2.4058 3.7610 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8153 -0.0379 3.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5192 -1.1332 1.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3354 -3.2178 2.8691 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -3.9486 1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5194 -3.0709 1.5549 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9619 -1.7011 2.5116 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8617 -3.3996 -0.6672 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2149 -2.0573 -1.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4395 -2.6236 -0.6206 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9462 -4.2892 0.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9520 1.5925 0.3096 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0287 0.5551 -2.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2724 3.0911 0.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9889 4.8469 0.5616 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6267 3.5011 -3.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9146 1.7353 -3.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7423 5.1762 -0.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3042 1.2905 -2.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5721 2.2858 0.7548 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4312 2.7332 -1.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2224 4.1391 -0.1082 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7044 3.6788 -1.7951 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3932 -2.4615 -2.9600 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 1 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 6 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 1 49 1 0 2 50 1 6 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 9 59 1 0 9 60 1 0 9 61 1 0 11 62 1 0 12 63 1 0 12 64 1 0 13 65 1 1 15 66 1 0 15 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 17 71 1 6 18 72 1 1 20 73 1 0 20 74 1 0 20 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 23 79 1 1 24 80 1 0 24 81 1 0 25 82 1 0 25 83 1 0 27 84 1 0 27 85 1 0 27 86 1 0 28 87 1 0 32 88 1 0 33 89 1 0 35 90 1 0 36 91 1 0 38 92 1 0 39 93 1 0 40 94 1 0 41 95 1 6 42 96 1 1 43 97 1 0 43 98 1 0 43 99 1 0 46100 1 0 M END

Standard InCHIKey	STMRENAXEMBDSK-KJVBOBAHSA-N
Standard InCHI	InChI=1S/C39H54O7/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/h7-12,14,23-24,28-30,32-33,40-41,43H,13,15-22H2,1-6H3,(H,44,45)/b14-9+/t23-,24+,28-,29-,30-,32+,33+,35+,36+,37-,38-,39+/m1/s1
SMILES	C[C@@H]1CC[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:	634.39	Volume:	674.838 ? Van der Waals volume.
Dense:	0.94	LogP:	4.012 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.599 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.146 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
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:	0.156	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.212	Fsp³:	0.692
MCE-18:	162.273 ? 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:	0.975	Fluc inhibitor:	0.986 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.274 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.013 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.105	Promiscuous compounds:	0.072

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.636	MDCK Permeability:	-5.166
Pgp-inhibitor:	0.117	Pgp-substrate:	0.009
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):	0.005
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	0.891
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08	MRP1:	0.428
Plasma Protein Binding (PPB):	83.378%	Volume Distribution (VD):	-0.152
Fu:	11.597% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.724	BCRP inhibitor:	0.036
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.862
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
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):

2.078

Half-life (T1/2):

1.547

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.046
Human Hepatotoxicity (H-HT):	0.754	Drug-induced Liver Injury (DILI):	0.715
AMES Toxicity:	0.368	Rat Oral Acute Toxicity:	0.215
Maximum Recommended Daily Dose:	0.387	Skin Sensitization:	0.993
Carcinogencity:	0.805	Eye Corrosion:	0.001
Eye Irritation:	0.36	Respiratory Toxicity:	0.659
Drug-induced Neurotoxicity:	0.051	Ototoxicity:	0.726
Hematotoxicity:	0.488	Drug-induced Nephrotoxicity:	0.945
Genotoxicity:	0.651	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.33	Hek293 Cytotoxicity:	0.411
BCF:	0.561 ? 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:	3.77 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.369 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.715 ? 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	=	67.2	%	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 NPC479744 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	7406
0.1-0.2	36861
0.2-0.3	4926
0.3-0.4	469
0.4-0.5	120
0.5-0.6	47
0.6-0.7	16
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	NPC479739
0.7826	Intermediate Similarity	NPC178093
0.7717	Intermediate Similarity	NPC304110
0.7717	Intermediate Similarity	NPC27518
0.7717	Intermediate Similarity	NPC611516
0.7113	Intermediate Similarity	NPC479745
0.7083	Intermediate Similarity	NPC479747
0.7083	Intermediate Similarity	NPC479746
0.6907	Remote Similarity	NPC475482
0.6667	Remote Similarity	NPC118033
0.6667	Remote Similarity	NPC324798
0.6667	Remote Similarity	NPC479742
0.6633	Remote Similarity	NPC132126
0.6531	Remote Similarity	NPC172311
0.6531	Remote Similarity	NPC54627
0.6531	Remote Similarity	NPC249817
0.6489	Remote Similarity	NPC485587
0.6421	Remote Similarity	NPC173569
0.6364	Remote Similarity	NPC482052
0.6327	Remote Similarity	NPC22676
0.63	Remote Similarity	NPC25491
0.62	Remote Similarity	NPC605663
0.6058	Remote Similarity	NPC479740
0.6058	Remote Similarity	NPC479741
0.59	Remote Similarity	NPC486700
0.59	Remote Similarity	NPC275312
0.5784	Remote Similarity	NPC198621
0.5784	Remote Similarity	NPC216940
0.5769	Remote Similarity	NPC482049
0.5769	Remote Similarity	NPC482050
0.5743	Remote Similarity	NPC475457
0.5714	Remote Similarity	NPC482051
0.5682	Remote Similarity	NPC61543
0.5682	Remote Similarity	NPC293048
0.5682	Remote Similarity	NPC225585
0.5648	Remote Similarity	NPC310729
0.5648	Remote Similarity	NPC150310
0.5644	Remote Similarity	NPC477874
0.5618	Remote Similarity	NPC32407
0.5618	Remote Similarity	NPC263548
0.5618	Remote Similarity	NPC606320
0.5591	Remote Similarity	NPC230151
0.5495	Remote Similarity	NPC481235
0.5455	Remote Similarity	NPC481234
0.5455	Remote Similarity	NPC479431
0.5444	Remote Similarity	NPC173089
0.5393	Remote Similarity	NPC51700
0.5393	Remote Similarity	NPC88716
0.5393	Remote Similarity	NPC68160
0.5385	Remote Similarity	NPC485589
0.5385	Remote Similarity	NPC488215
0.5364	Remote Similarity	NPC601567
0.5364	Remote Similarity	NPC606631
0.5333	Remote Similarity	NPC487491
0.5333	Remote Similarity	NPC262970
0.5327	Remote Similarity	NPC487490
0.5319	Remote Similarity	NPC485588
0.5288	Remote Similarity	NPC171007
0.5288	Remote Similarity	NPC190849
0.5283	Remote Similarity	NPC488214
0.5278	Remote Similarity	NPC610795
0.5208	Remote Similarity	NPC54909
0.5204	Remote Similarity	NPC485585
0.52	Remote Similarity	NPC485882
0.5165	Remote Similarity	NPC71074
0.5165	Remote Similarity	NPC605937
0.5158	Remote Similarity	NPC485586
0.5109	Remote Similarity	NPC87095
0.5094	Remote Similarity	NPC477873
0.5091	Remote Similarity	NPC475454
0.5091	Remote Similarity	NPC473579

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3546
0.1-0.2	5508
0.2-0.3	93
0.3-0.4	2
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