NPASS Compound

Natural Product: NPC479793

Natural Product ID	NPC479793
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HNUOYOLLTWHUQG-BSAQFQISSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	132525314
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 101107 0 0 0 0 0 0 0 0999 V2000 -7.8317 3.2427 3.1493 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2019 1.9509 2.7068 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2844 0.8947 2.4679 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3992 2.1791 1.5030 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3475 3.3257 0.9979 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6220 1.1245 0.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3122 0.9422 1.2472 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5449 -0.0197 0.6438 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1429 -0.2323 0.9644 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1168 0.4615 0.1730 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8543 1.8025 0.1508 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1889 2.3399 -0.6166 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0027 1.5372 -1.3867 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7609 0.2012 -1.3784 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6050 -0.7636 -2.1353 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7647 -0.1665 -2.8019 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7549 0.0724 -4.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8156 0.6283 -4.8478 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9521 0.9670 -4.1465 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0065 0.7474 -2.7951 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2074 1.0969 -1.9867 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4290 -0.0080 -0.9760 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2237 -0.2210 -0.1032 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3271 0.6320 1.1037 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8554 0.0823 2.2478 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9807 0.8077 3.4304 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5659 2.1229 3.4733 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0378 2.6736 2.3311 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9149 1.9447 1.1526 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6097 3.9995 2.3409 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6875 2.8616 4.6598 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0085 -0.0182 -0.7916 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9369 0.1920 -2.1321 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4863 0.3226 -0.1142 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0653 1.5311 -4.7604 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6245 -0.2574 -4.8955 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9749 -1.8686 -1.1695 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6838 -2.5728 -0.8179 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8251 -3.4146 0.3912 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6042 -2.9301 1.6639 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7617 -3.7520 2.7828 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1369 -5.0490 2.6375 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3638 -5.5562 1.3759 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2038 -4.7306 0.2730 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7446 -6.8849 1.2869 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2851 -5.8455 3.7918 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4200 -1.7037 -0.6958 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2644 -0.3336 -0.6271 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8019 -2.7877 -1.7748 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0401 2.0875 -2.1494 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6014 2.7072 0.8856 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1273 -0.7692 -0.3648 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4243 -0.5739 -0.7673 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0587 -1.3856 -1.8645 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2025 0.3890 -0.1734 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5344 0.6049 -0.5760 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7955 1.5306 -1.6017 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4077 -1.7822 -1.0359 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8262 1.7542 2.2950 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9552 3.1613 3.1545 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6031 4.1053 2.4927 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4951 3.5370 4.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5126 1.5964 3.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8894 0.8216 3.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9963 1.2537 1.6981 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8560 -0.0890 2.2790 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9432 -1.3416 0.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9129 -0.0394 2.0499 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3637 3.4117 -0.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9548 -1.2262 -2.9046 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8030 0.8140 -5.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1254 2.0558 -1.4667 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1141 1.1332 -2.6258 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6812 -0.9612 -1.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2460 -1.3061 0.2332 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1921 -0.9424 2.2622 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3976 0.3792 4.3354 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4983 2.3693 0.2521 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2741 4.7614 2.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5387 3.3448 4.9307 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7702 1.2602 -0.1943 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2249 2.5157 -4.7577 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6952 0.0449 -4.7291 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3645 -1.5010 -0.1969 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4487 -3.2072 -1.7235 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3048 -1.8954 1.7523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5612 -3.2746 3.7369 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3841 -5.1352 -0.7066 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1998 -7.3089 0.5146 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5857 -6.8229 3.6511 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4017 -3.2575 -1.1686 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5349 2.8848 -1.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8875 3.5847 0.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1223 -1.5346 -1.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6231 -2.3882 -1.9530 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9928 -0.8843 -2.8435 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8999 2.1484 -1.7697 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6190 2.1934 -1.2404 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0888 1.0214 -2.5412 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7769 -2.7119 -1.1693 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4081 1.2989 3.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 23 32 1 0 32 33 1 0 22 34 1 0 19 35 1 0 17 36 1 0 15 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 43 45 1 0 42 46 1 0 38 47 1 0 47 48 1 0 37 49 1 0 13 50 1 0 11 51 1 0 8 52 2 0 52 53 1 0 53 54 1 0 53 55 2 0 55 56 1 0 56 57 1 0 52 58 1 0 7 59 1 0 55 6 1 0 48 10 1 0 48 14 2 0 33 16 1 0 44 39 1 0 33 20 2 0 29 24 1 0 1 60 1 0 1 61 1 0 1 62 1 0 2 63 1 0 3 64 1 0 3 65 1 0 3 66 1 0 9 67 1 0 9 68 1 0 12 69 1 0 15 70 1 6 18 71 1 0 21 72 1 0 21 73 1 0 22 74 1 6 23 75 1 1 25 76 1 0 26 77 1 0 29 78 1 0 30 79 1 0 31 80 1 0 34 81 1 0 35 82 1 0 36 83 1 0 37 84 1 1 38 85 1 6 40 86 1 0 41 87 1 0 44 88 1 0 45 89 1 0 46 90 1 0 49 91 1 0 50 92 1 0 51 93 1 0 54 94 1 0 54 95 1 0 54 96 1 0 57 97 1 0 57 98 1 0 57 99 1 0 58100 1 0 59101 1 0 M END

Standard InCHIKey	HNUOYOLLTWHUQG-BSAQFQISSA-N
Standard InCHI	InChI=1S/C43H42O16/c1-15(2)35(53)34-37(55)21(36(54)16(3)39(34)57-4)11-19-24(46)13-28(50)31-33(38(56)41(59-42(19)31)18-6-8-23(45)27(49)10-18)32-29(51)14-25(47)20-12-30(52)40(58-43(20)32)17-5-7-22(44)26(48)9-17/h5-10,13-15,30,33,38,40-41,44-52,54-56H,11-12H2,1-4H3/t30-,33+,38+,40-,41-/m1/s1
SMILES	CC(C)C(=O)c1c(c(Cc2c(cc(c3[C@@H](c4c(cc(c5C[C@H]([C@@H](c6ccc(c(c6)O)O)Oc45)O)O)O)[C@@H]([C@@H](c4ccc(c(c4)O)O)Oc23)O)O)O)c(c(C)c1OC)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	814.25	Volume:	790.849 ? Van der Waals volume.
Dense:	1.03	LogP:	1.957 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.231 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.916 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	41.0
TPSA:	287.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	12.0	Rings:	7.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.071	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.206	Fsp³:	0.279
MCE-18:	160.909 ? 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:	0.819	Fluc inhibitor:	0.143 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.726 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.668 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.174	Promiscuous compounds:	0.096

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.566	MDCK Permeability:	-5.06
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.815 ? 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):	0.006
20% Bioavailability (F20%):	0.992	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	95.51%	Volume Distribution (VD):	0.095
Fu:	6.022% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.0
BSEP inhibitor:	0.085

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.138	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

4.448

Half-life (T1/2):

5.655

ADMET: Toxicity

hERG Blockers:	0.073	hERG Blockers (10um):	0.855
Human Hepatotoxicity (H-HT):	0.913	Drug-induced Liver Injury (DILI):	0.605
AMES Toxicity:	0.186	Rat Oral Acute Toxicity:	0.464
Maximum Recommended Daily Dose:	0.988	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.09	Respiratory Toxicity:	0.996
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.992
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	0.089
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.097
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.989
BCF:	1.211 ? 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:	4.73 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.023 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.532 ? 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
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22281186]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588326]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18007	Agrimonia pilosa	Species	Rosaceae	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
Cell line	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
NPT34	Cell line	BV-2	Mus musculus	IC50	=	38100.0	nM	PMID[27588326]

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 NPC479793 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	13272
0.1-0.2	33262
0.2-0.3	3137
0.3-0.4	117
0.4-0.5	36
0.5-0.6	28
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8519	High Similarity	NPC479794
0.84	Intermediate Similarity	NPC183811
0.7821	Intermediate Similarity	NPC223148
0.7532	Intermediate Similarity	NPC142252
0.7073	Intermediate Similarity	NPC297222
0.5732	Remote Similarity	NPC58190
0.5732	Remote Similarity	NPC108811
0.5732	Remote Similarity	NPC170103
0.5732	Remote Similarity	NPC236202
0.5732	Remote Similarity	NPC262911
0.5732	Remote Similarity	NPC202742
0.5663	Remote Similarity	NPC246202
0.5663	Remote Similarity	NPC224161
0.5663	Remote Similarity	NPC46335
0.5663	Remote Similarity	NPC279406
0.5663	Remote Similarity	NPC486519
0.5568	Remote Similarity	NPC278548
0.5349	Remote Similarity	NPC313116
0.5349	Remote Similarity	NPC603340
0.5227	Remote Similarity	NPC70409
0.5227	Remote Similarity	NPC204770
0.5227	Remote Similarity	NPC600551
0.5227	Remote Similarity	NPC601980
0.5227	Remote Similarity	NPC602065
0.5227	Remote Similarity	NPC611024
0.5169	Remote Similarity	NPC226809
0.5111	Remote Similarity	NPC600630
0.5111	Remote Similarity	NPC607896
0.5111	Remote Similarity	NPC611369
0.5057	Remote Similarity	NPC165483
0.5057	Remote Similarity	NPC184245
0.5057	Remote Similarity	NPC187801
0.5057	Remote Similarity	NPC610920

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3140
0.1-0.2	5949
0.2-0.3	58
0.3-0.4	3
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