NPASS Compound

Natural Product: NPC479747

Natural Product ID	NPC479747
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ADBNLBJPUAZWEK-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 -7.9988 -1.3857 2.2185 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3101 -0.7750 1.0299 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7967 -1.2762 -0.2842 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6938 -1.8935 -1.0686 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5315 -0.9105 -1.3009 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4161 -1.7436 -1.8236 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0743 -1.1189 -1.8827 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6903 -0.4871 -0.5959 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1298 -1.5157 0.3676 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7992 0.1840 0.1247 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4929 1.1474 0.9830 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1131 1.6147 1.2864 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1056 0.9852 0.4190 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2457 1.6978 0.3364 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1500 3.0563 -0.2504 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6224 1.8844 1.7950 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1127 2.0956 1.9414 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8927 1.0343 1.2650 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6150 0.8577 -0.2155 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2136 1.8674 -1.1017 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1607 -0.5355 -0.5059 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4604 -0.8081 -0.2338 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6269 -0.4298 -0.7307 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6805 0.3595 -1.6983 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9231 -0.9156 -0.1746 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0341 -0.5095 -0.7066 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3233 -0.9521 -0.2035 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4756 -0.4781 -0.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7146 -0.8472 -0.4097 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8333 -1.7154 0.6532 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7227 -2.1956 1.2793 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4460 -1.8119 0.8491 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0970 -2.1034 1.0885 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1157 0.7284 -0.3832 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6912 0.6396 -1.8301 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6842 0.0208 -1.8626 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 0.6138 -0.9077 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3957 1.7296 -1.5981 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2477 1.2123 1.5131 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3921 2.0210 3.3070 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2280 -0.1551 -0.0437 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8006 -0.9666 1.0955 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3704 -0.5156 2.4573 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9893 0.0023 -2.3646 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0790 1.2209 -2.1407 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3125 -0.5098 -3.5971 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5894 -2.3672 2.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9320 -0.6429 3.0567 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0589 -1.5389 1.9622 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4909 0.3257 1.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3914 -0.5446 -0.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5251 -2.1101 -0.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0953 -2.1118 -2.1010 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3488 -2.8602 -0.6850 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6913 -2.0415 -2.8785 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4010 -2.7334 -1.2777 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3446 -1.9746 -2.0389 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0117 -0.4556 -2.7528 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3140 -1.2583 1.4317 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1079 -1.8322 0.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7549 -2.4478 0.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3276 1.6534 1.5235 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1260 2.7218 1.3210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9637 1.3319 2.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8170 0.0111 0.9267 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1826 3.1599 -1.3247 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9643 3.6868 0.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7739 3.5702 0.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0976 2.7757 2.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3248 1.0218 2.4208 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3834 3.1222 1.6179 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6132 0.0563 1.7531 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1724 2.2295 -0.6833 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5262 2.7539 -1.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4028 1.5060 -2.1293 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9027 -0.8038 -1.5882 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5394 -1.3011 0.0588 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8906 -1.5808 0.6422 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0219 0.1891 -1.5631 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3850 0.1956 -1.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6018 -0.4786 -0.8911 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8189 -2.8786 2.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6097 -2.2142 1.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2265 -2.7968 1.8005 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8701 -0.2914 0.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3545 -0.0653 -2.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7575 1.5834 -2.3894 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0826 0.1725 -2.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5521 -1.0732 -1.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3454 1.4065 -2.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6798 2.5516 -0.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7954 2.2036 -2.4169 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4506 2.1443 1.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3290 2.2316 3.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7898 0.8021 -0.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5350 -2.0483 0.9937 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7506 -1.3147 3.1630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9277 0.3994 2.7826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2973 -0.4799 2.6315 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7312 0.0224 -4.3487 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 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 19 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 6 18 39 1 0 17 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 37 8 1 0 37 13 1 0 34 14 1 0 32 27 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 25 78 1 0 26 79 1 0 28 80 1 0 29 81 1 0 31 82 1 0 32 83 1 0 33 84 1 0 34 85 1 1 35 86 1 0 35 87 1 0 36 88 1 0 36 89 1 0 38 90 1 0 38 91 1 0 38 92 1 0 39 93 1 0 40 94 1 0 41 95 1 6 42 96 1 6 43 97 1 0 43 98 1 0 43 99 1 0 46100 1 0 M END

Standard InCHIKey	ADBNLBJPUAZWEK-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(41)33(43)36(4,29(35)16-17-38(30,37)6)22-46-31(42)14-9-25-7-10-26(40)11-8-25/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)(COC(=O)/C=C/c6ccc(cc6)O)[C@@H]5CC[C@@]34C)O)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:	4.068 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.489 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.318 ? 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:	5.181	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:	0.972	Fluc inhibitor:	0.974 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.248 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.104	Promiscuous compounds:	0.062

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.573	MDCK Permeability:	-5.107
Pgp-inhibitor:	0.036	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):	0.001
20% Bioavailability (F20%):	0.892	30% Bioavailability (F30%):	0.7
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068	MRP1:	0.475
Plasma Protein Binding (PPB):	94.684%	Volume Distribution (VD):	-0.485
Fu:	3.482% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.973	BCRP inhibitor:	0.015
BSEP inhibitor:	0.997

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:	0.049
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.708
HLM stability:	0.001 ? 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):

1.863

Half-life (T1/2):

1.711

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.049
Human Hepatotoxicity (H-HT):	0.676	Drug-induced Liver Injury (DILI):	0.809
AMES Toxicity:	0.363	Rat Oral Acute Toxicity:	0.12
Maximum Recommended Daily Dose:	0.518	Skin Sensitization:	0.953
Carcinogencity:	0.757	Eye Corrosion:	0.0
Eye Irritation:	0.26	Respiratory Toxicity:	0.536
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.772
Hematotoxicity:	0.386	Drug-induced Nephrotoxicity:	0.932
Genotoxicity:	0.843	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.098	Hek293 Cytotoxicity:	0.302
BCF:	0.579 ? 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:	3.787 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.356 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.722 ? 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	=	67.0	%	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 NPC479747 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	7998
0.1-0.2	36739
0.2-0.3	4532
0.3-0.4	405
0.4-0.5	109
0.5-0.6	44
0.6-0.7	17
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC479746
0.837	Intermediate Similarity	NPC479740
0.837	Intermediate Similarity	NPC479741
0.8242	Intermediate Similarity	NPC482049
0.8242	Intermediate Similarity	NPC482050
0.7368	Intermediate Similarity	NPC304110
0.7368	Intermediate Similarity	NPC27518
0.7368	Intermediate Similarity	NPC611516
0.7292	Intermediate Similarity	NPC178093
0.7263	Intermediate Similarity	NPC54627
0.7263	Intermediate Similarity	NPC249817
0.7113	Intermediate Similarity	NPC475482
0.7083	Intermediate Similarity	NPC479744
0.6979	Remote Similarity	NPC198621
0.6979	Remote Similarity	NPC216940
0.6634	Remote Similarity	NPC479745
0.6381	Remote Similarity	NPC118033
0.6286	Remote Similarity	NPC310729
0.6286	Remote Similarity	NPC150310
0.6214	Remote Similarity	NPC324798
0.6214	Remote Similarity	NPC479742
0.6186	Remote Similarity	NPC139243
0.6186	Remote Similarity	NPC116742
0.6092	Remote Similarity	NPC71074
0.6092	Remote Similarity	NPC605937
0.6078	Remote Similarity	NPC172311
0.6023	Remote Similarity	NPC32407
0.6023	Remote Similarity	NPC263548
0.6023	Remote Similarity	NPC606320
0.6019	Remote Similarity	NPC25491
0.598	Remote Similarity	NPC262970
0.5962	Remote Similarity	NPC479739
0.5922	Remote Similarity	NPC605663
0.5905	Remote Similarity	NPC473773
0.5905	Remote Similarity	NPC475579
0.5859	Remote Similarity	NPC485587
0.58	Remote Similarity	NPC173569
0.5784	Remote Similarity	NPC475457
0.5769	Remote Similarity	NPC482052
0.5619	Remote Similarity	NPC488214
0.5588	Remote Similarity	NPC235557
0.5577	Remote Similarity	NPC22676
0.5495	Remote Similarity	NPC87095
0.5474	Remote Similarity	NPC230151
0.5463	Remote Similarity	NPC482051
0.5444	Remote Similarity	NPC51700
0.5444	Remote Similarity	NPC88716
0.5444	Remote Similarity	NPC68160
0.5421	Remote Similarity	NPC145527
0.5421	Remote Similarity	NPC208785
0.5333	Remote Similarity	NPC271494
0.5326	Remote Similarity	NPC305464
0.5326	Remote Similarity	NPC19376
0.5326	Remote Similarity	NPC25848
0.5221	Remote Similarity	NPC481234
0.5221	Remote Similarity	NPC479431
0.5217	Remote Similarity	NPC61543
0.5217	Remote Similarity	NPC293048
0.5217	Remote Similarity	NPC225585
0.5217	Remote Similarity	NPC37221
0.5179	Remote Similarity	NPC206232
0.5179	Remote Similarity	NPC14515
0.5161	Remote Similarity	NPC173089
0.5138	Remote Similarity	NPC132126
0.5138	Remote Similarity	NPC606782
0.5135	Remote Similarity	NPC475454
0.5135	Remote Similarity	NPC473579
0.5133	Remote Similarity	NPC601567
0.5133	Remote Similarity	NPC606631
0.5102	Remote Similarity	NPC96693
0.51	Remote Similarity	NPC485585
0.5094	Remote Similarity	NPC477874
0.5047	Remote Similarity	NPC171007
0.5047	Remote Similarity	NPC190849

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3492
0.1-0.2	5570
0.2-0.3	86
0.3-0.4	1
0.4-0.5	0
0.5-0.6	1
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
0.5138	Remote Similarity	NPD8166	Discontinued

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