NPASS Compound

Natural Product: NPC479745

Natural Product ID	NPC479745
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IPAQLBIWWREMRV-AXWOZBRASA-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 101106 0 0 0 0 0 0 0 0999 V2000 -7.3705 -2.8873 -0.6302 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9270 -1.7458 0.2670 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5932 -0.4841 -0.3024 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3593 0.6327 0.6431 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9518 0.8320 1.1157 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3998 2.0272 0.4148 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9358 2.2881 0.6035 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1111 1.0548 0.2023 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3674 0.9023 -1.2667 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6435 -0.0183 1.0518 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8381 -0.6761 1.8418 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 -0.4651 1.9985 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9312 0.0310 0.6253 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5435 -0.0495 0.4793 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3400 0.3194 1.6882 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -1.5384 0.2240 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3250 -1.7434 0.0015 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8901 -0.9189 -1.0864 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3772 0.4789 -1.2183 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3413 1.5013 -0.6757 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3690 0.7215 -2.7472 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5396 -0.1854 -3.3817 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9741 0.6360 -0.7862 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4548 2.0561 -0.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0342 1.9151 -0.8833 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6312 1.3026 0.3672 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4935 2.3509 1.4448 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3050 -0.8153 -0.8596 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2473 -1.3532 -1.7058 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8624 -1.9598 -2.7188 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6560 -1.1881 -1.3768 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0375 -0.5408 -0.2954 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4295 -0.3476 0.0792 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7485 0.3489 1.2422 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0464 0.5645 1.6502 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1003 0.0894 0.9078 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7992 -0.6062 -0.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4975 -0.8141 -0.6483 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8734 -1.0805 -0.9931 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4143 0.2998 1.3080 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4705 -3.1054 -0.3567 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0777 -0.3888 1.0662 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4365 -1.4560 0.0960 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6956 -2.7323 0.5239 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0782 1.2314 2.5555 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6749 2.3331 3.0034 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6623 0.3810 3.4885 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4521 -2.7099 -0.8428 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8437 -2.7852 -1.6046 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2470 -3.8724 -0.1606 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2074 -1.8871 1.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6770 -0.7131 -0.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2395 -0.3217 -1.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0795 0.4764 1.5016 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7522 1.5719 0.1544 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7321 2.1162 -0.6424 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9101 2.9309 0.8837 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6927 3.1460 -0.0592 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8027 2.5324 1.6745 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0706 1.8690 -1.7329 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8736 0.0653 -1.7525 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4402 0.8267 -1.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2572 -1.4703 2.4665 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1896 0.2607 2.8051 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 -1.3913 2.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3693 -0.7071 -0.1167 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1664 1.0177 1.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8031 -0.5689 2.2145 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7175 0.7842 2.4800 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3188 -1.8098 -0.6955 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5429 -2.1804 1.0447 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9407 -1.6226 0.9046 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7999 -1.5039 -2.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0596 1.0486 0.0715 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8437 2.4002 -0.3154 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0394 1.8434 -1.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1091 1.7625 -2.9840 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4046 0.5236 -3.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0586 -0.8796 -3.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3566 0.1242 -1.5894 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7966 2.5403 -1.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8083 2.6561 0.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4397 2.9088 -1.1165 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1826 1.1699 -1.7210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9559 2.0917 2.4043 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4706 2.6712 1.6407 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9967 3.2783 1.0361 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3816 -1.6157 -2.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2751 -0.1340 0.3436 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9144 0.7309 1.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2459 1.1210 2.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3217 -1.3601 -1.5569 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0699 -0.6559 -1.8833 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8828 1.1545 0.9852 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2993 -3.6515 0.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3326 -0.9397 2.0318 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2492 -1.3283 -0.9405 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9573 -3.5653 -0.1647 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6178 -2.5341 0.3530 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8868 -2.9821 1.5794 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2838 0.3698 4.4392 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 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 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 1 18 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 37 39 1 0 36 40 1 0 17 41 1 0 10 42 1 0 42 43 1 0 43 44 1 0 5 45 1 1 45 46 2 0 45 47 1 0 43 2 1 0 42 5 1 0 26 8 1 0 38 33 1 0 26 13 1 0 23 14 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 1 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 9 60 1 0 9 61 1 0 9 62 1 0 11 63 1 0 12 64 1 0 12 65 1 0 13 66 1 6 15 67 1 0 15 68 1 0 15 69 1 0 16 70 1 0 16 71 1 0 17 72 1 1 18 73 1 6 20 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 21 78 1 0 22 79 1 0 23 80 1 6 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 27 85 1 0 27 86 1 0 27 87 1 0 31 88 1 0 32 89 1 0 34 90 1 0 35 91 1 0 38 92 1 0 39 93 1 0 40 94 1 0 41 95 1 0 42 96 1 1 43 97 1 6 44 98 1 0 44 99 1 0 44100 1 0 47101 1 0 M END

Standard InCHIKey	IPAQLBIWWREMRV-AXWOZBRASA-N
Standard InCHI	InChI=1S/C39H54O8/c1-22-13-16-39(34(45)46)18-17-37(5)25(32(39)23(22)2)9-11-30-35(3)20-28(43)33(36(4,21-40)29(35)14-15-38(30,37)6)47-31(44)12-8-24-7-10-26(41)27(42)19-24/h7-10,12,19,22-23,28-30,32-33,40-43H,11,13-18,20-21H2,1-6H3,(H,45,46)/b12-8+/t22-,23+,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)OC(=O)/C=C/c3ccc(c(c3)O)O)O)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.38	Volume:	683.628 ? Van der Waals volume.
Dense:	0.951	LogP:	4.381 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.644 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.453 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	144.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.102	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.291	Fsp³:	0.692
MCE-18:	165.879 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.927	Fluc inhibitor:	0.984 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.333 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.015 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.098	Promiscuous compounds:	0.142

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.716	MDCK Permeability:	-5.203
Pgp-inhibitor:	0.03	Pgp-substrate:	0.001
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):	0.003
20% Bioavailability (F20%):	0.961	30% Bioavailability (F30%):	0.81
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031	MRP1:	0.69
Plasma Protein Binding (PPB):	87.187%	Volume Distribution (VD):	-0.463
Fu:	10.877% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.943	BCRP inhibitor:	0.045
BSEP inhibitor:	0.973

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:	0.001	CYP3A4-substrate:	0.982
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.245
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):

3.637

Half-life (T1/2):

1.612

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.071
Human Hepatotoxicity (H-HT):	0.601	Drug-induced Liver Injury (DILI):	0.782
AMES Toxicity:	0.233	Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.404	Skin Sensitization:	0.997
Carcinogencity:	0.734	Eye Corrosion:	0.003
Eye Irritation:	0.589	Respiratory Toxicity:	0.595
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.889
Hematotoxicity:	0.212	Drug-induced Nephrotoxicity:	0.764
Genotoxicity:	0.738	RPMI-8226 Immunitoxicity:	0.009
A549 Cytotoxicity:	0.36	Hek293 Cytotoxicity:	0.134
BCF:	0.606 ? 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:	3.71 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.454 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.726 ? 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	=	72.8	%	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 NPC479745 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	7648
0.1-0.2	36834
0.2-0.3	4638
0.3-0.4	555
0.4-0.5	100
0.5-0.6	54
0.6-0.7	18
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC178093
0.8352	Intermediate Similarity	NPC304110
0.8352	Intermediate Similarity	NPC27518
0.8352	Intermediate Similarity	NPC611516
0.7789	Intermediate Similarity	NPC324798
0.7789	Intermediate Similarity	NPC479742
0.7755	Intermediate Similarity	NPC118033
0.7604	Intermediate Similarity	NPC482051
0.7113	Intermediate Similarity	NPC479744
0.6869	Remote Similarity	NPC25491
0.6768	Remote Similarity	NPC605663
0.6634	Remote Similarity	NPC479747
0.6634	Remote Similarity	NPC479746
0.6556	Remote Similarity	NPC230151
0.6415	Remote Similarity	NPC481234
0.6415	Remote Similarity	NPC479431
0.6392	Remote Similarity	NPC485587
0.6373	Remote Similarity	NPC132126
0.6364	Remote Similarity	NPC26045
0.6327	Remote Similarity	NPC173569
0.6321	Remote Similarity	NPC601567
0.6321	Remote Similarity	NPC606631
0.63	Remote Similarity	NPC171007
0.63	Remote Similarity	NPC190849
0.6275	Remote Similarity	NPC482052
0.6154	Remote Similarity	NPC479739
0.6078	Remote Similarity	NPC22676
0.5962	Remote Similarity	NPC172311
0.5849	Remote Similarity	NPC475482
0.5833	Remote Similarity	NPC479740
0.5833	Remote Similarity	NPC479741
0.581	Remote Similarity	NPC54627
0.581	Remote Similarity	NPC249817
0.5769	Remote Similarity	NPC477873
0.5686	Remote Similarity	NPC182249
0.5686	Remote Similarity	NPC473591
0.5686	Remote Similarity	NPC155192
0.5472	Remote Similarity	NPC101863
0.5446	Remote Similarity	NPC310729
0.5446	Remote Similarity	NPC150310
0.5413	Remote Similarity	NPC482049
0.5413	Remote Similarity	NPC482050
0.5376	Remote Similarity	NPC32407
0.5376	Remote Similarity	NPC263548
0.5376	Remote Similarity	NPC606320
0.537	Remote Similarity	NPC488214
0.5319	Remote Similarity	NPC485589
0.5306	Remote Similarity	NPC233012
0.5304	Remote Similarity	NPC53520
0.53	Remote Similarity	NPC485585
0.5294	Remote Similarity	NPC485882
0.5278	Remote Similarity	NPC198621
0.5278	Remote Similarity	NPC216940
0.5269	Remote Similarity	NPC71074
0.5269	Remote Similarity	NPC605937
0.5258	Remote Similarity	NPC485588
0.5243	Remote Similarity	NPC177246
0.5225	Remote Similarity	NPC610795
0.5213	Remote Similarity	NPC173089
0.5185	Remote Similarity	NPC488215
0.5182	Remote Similarity	NPC606782
0.5172	Remote Similarity	NPC481235
0.5161	Remote Similarity	NPC51700
0.5161	Remote Similarity	NPC88716
0.5161	Remote Similarity	NPC68160
0.5146	Remote Similarity	NPC57362
0.514	Remote Similarity	NPC477874
0.5138	Remote Similarity	NPC487491
0.5135	Remote Similarity	NPC487490
0.5106	Remote Similarity	NPC61543
0.5106	Remote Similarity	NPC293048
0.5106	Remote Similarity	NPC225585
0.5102	Remote Similarity	NPC485586
0.5096	Remote Similarity	NPC470617
0.5096	Remote Similarity	NPC470616
0.5094	Remote Similarity	NPC252133
0.5094	Remote Similarity	NPC43353
0.5093	Remote Similarity	NPC271494
0.5093	Remote Similarity	NPC475457
0.5053	Remote Similarity	NPC87095
0.5047	Remote Similarity	NPC475138

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3672
0.1-0.2	5399
0.2-0.3	76
0.3-0.4	2
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
0.5182	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