NPASS Compound

Natural Product: NPC274411

Natural Product ID	NPC274411
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UKUKDKRGVVIVIE-BSHMMWLWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10078117
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 105110 0 0 0 0 0 0 0 0999 V2000 -8.1270 1.3189 1.5277 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1507 1.2553 0.3734 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1767 2.5816 -0.3313 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6093 0.1706 -0.5817 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0076 -1.1672 -0.2182 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4768 -1.1745 -0.4292 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0511 0.2454 -0.3180 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7328 0.9118 0.8615 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5972 0.3007 -0.2504 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9821 1.2471 -0.9522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5304 1.3992 -0.9577 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8774 0.0603 -0.9767 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6517 0.1771 -0.8297 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2802 -0.9751 -1.5367 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1500 1.4268 -1.5191 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6297 1.5653 -1.4023 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2355 1.1261 -0.1033 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1852 1.0588 0.9842 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7279 0.5247 2.2768 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8827 2.5460 1.2889 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9394 0.3541 0.6015 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6780 -0.9593 1.2838 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5362 -1.6509 0.8488 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4856 -0.9883 -0.1141 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8562 -2.1246 -1.0927 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7901 -0.6095 0.5695 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4898 0.2411 1.8349 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5372 -1.7955 1.0923 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8416 -2.1295 0.4899 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8166 -2.4239 1.4913 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0479 0.0252 -0.1903 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3858 0.2480 0.1004 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9262 -0.5382 1.2423 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9003 -1.6233 0.8559 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8473 -1.2529 -0.2333 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5065 0.1426 -0.7106 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3760 0.4770 -1.8495 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9017 0.7115 -2.9889 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7421 0.5368 -1.6723 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6474 0.8506 -2.7146 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1566 0.1218 -1.0599 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1888 -1.3822 0.1205 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1763 -2.7891 0.5659 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4842 0.3002 2.2349 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3523 -1.5447 -1.8898 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8140 -2.5891 -2.2965 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8573 -0.6927 -2.8710 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6920 0.3554 1.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6393 1.4484 2.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8892 2.0947 1.3124 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8198 2.4969 -1.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2216 2.9862 -0.2825 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5456 3.2778 0.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4405 0.4731 -1.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7037 0.0616 -0.4465 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5014 -1.9324 -0.8424 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2751 -1.3816 0.8338 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4113 0.7994 -1.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8642 0.2409 1.7082 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2550 1.8707 1.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6057 1.9396 -1.5491 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.9546 -1.9089 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1473 2.0852 -0.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9375 -0.2307 -2.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6522 -1.3190 -2.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4846 -1.8628 -0.9498 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2427 -0.7023 -2.0672 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6077 2.3129 -1.1910 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9161 1.2845 -2.6119 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1971 1.0780 -2.2501 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8363 2.6641 -1.5872 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9317 1.9632 0.2151 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8280 -0.5509 2.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1045 0.9629 3.1003 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7443 0.9828 2.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4067 2.9100 2.1683 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1175 3.1950 0.4472 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7717 2.6221 1.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1099 1.0188 1.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7173 -0.7530 2.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6121 -1.5743 1.1040 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2263 -2.6880 0.5084 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1390 -1.9068 1.7709 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9389 -2.6967 -1.3665 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6046 -2.8077 -0.7478 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2308 -1.7008 -2.0493 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5018 1.3063 1.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5712 -0.0341 2.3262 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3055 0.0698 2.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8939 -2.6994 1.1693 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7720 -1.6575 2.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7941 -3.1292 -0.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4714 -3.1162 2.0972 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4765 1.3415 0.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0837 -1.0574 1.7476 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5048 -1.8362 1.7813 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6200 -1.9302 -1.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7215 0.8793 0.0935 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6225 1.1083 -2.2537 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8466 -0.0340 -3.3654 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3280 1.6977 -3.3246 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4119 -2.3523 -0.0535 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2143 -3.4540 1.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2821 1.2457 1.9825 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6848 -0.8339 -3.8588 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 17 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 36 41 1 0 35 42 1 0 34 43 1 0 33 44 1 0 6 45 1 6 45 46 2 0 45 47 1 0 8 2 1 0 26 9 1 0 41 32 1 0 29 6 1 0 24 12 1 0 21 13 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 10 61 1 0 11 62 1 0 11 63 1 0 12 64 1 0 14 65 1 0 14 66 1 0 14 67 1 0 15 68 1 0 15 69 1 0 16 70 1 0 16 71 1 0 17 72 1 1 19 73 1 0 19 74 1 0 19 75 1 0 20 76 1 0 20 77 1 0 20 78 1 0 21 79 1 0 22 80 1 0 22 81 1 0 23 82 1 0 23 83 1 0 25 84 1 0 25 85 1 0 25 86 1 0 27 87 1 0 27 88 1 0 27 89 1 0 28 90 1 0 28 91 1 0 29 92 1 6 30 93 1 0 32 94 1 1 33 95 1 1 34 96 1 1 35 97 1 6 36 98 1 1 40 99 1 0 40100 1 0 40101 1 0 42102 1 0 43103 1 0 44104 1 0 47105 1 0 M END

Standard InCHIKey	UKUKDKRGVVIVIE-BSHMMWLWSA-N
Standard InCHI	InChI=1S/C37H58O10/c1-32(2)15-16-37(31(43)44)20(17-32)19-9-10-22-34(5)13-12-24(46-30-27(41)25(39)26(40)28(47-30)29(42)45-8)33(3,4)21(34)11-14-35(22,6)36(19,7)18-23(37)38/h9,20-28,30,38-41H,10-18H2,1-8H3,(H,43,44)/t20?,21?,22?,23-,24+,25+,26+,27-,28+,30-,34+,35-,36-,37-/m1/s1
SMILES	CC1(C)CC[C@]2(C(C1)C1=CCC3[C@@]4(C)CC[C@@H](C(C)(C)C4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)OC)O1)O)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	662.4	Volume:	677.162 ? Van der Waals volume.
Dense:	0.978	LogP:	2.746 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.935 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.536 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	34.0
TPSA:	162.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.167	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.405	Fsp³:	0.892
MCE-18:	133.0 ? 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:	0.878	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.026 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.16	Promiscuous compounds:	0.115

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.515	MDCK Permeability:	-5.154
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	0.994 ? 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):	0.002
20% Bioavailability (F20%):	0.014	30% Bioavailability (F30%):	0.063
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02	MRP1:	0.756
Plasma Protein Binding (PPB):	80.11%	Volume Distribution (VD):	-0.373
Fu:	18.052% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.0
BSEP inhibitor:	0.231

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.982
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.603
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):

0.807

Half-life (T1/2):

2.331

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.104
Human Hepatotoxicity (H-HT):	0.637	Drug-induced Liver Injury (DILI):	0.715
AMES Toxicity:	0.128	Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.248	Skin Sensitization:	0.899
Carcinogencity:	0.331	Eye Corrosion:	0.0
Eye Irritation:	0.019	Respiratory Toxicity:	0.158
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.873
Hematotoxicity:	0.06	Drug-induced Nephrotoxicity:	0.776
Genotoxicity:	0.344	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.066	Hek293 Cytotoxicity:	0.276
BCF:	1.673 ? 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:	4.606 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.076 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.47 ? 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
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20295	Eclipta prostrata	Species	Asteraceae	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

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

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 NPC274411 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	17401
0.1-0.2	27051
0.2-0.3	4068
0.3-0.4	893
0.4-0.5	325
0.5-0.6	86
0.6-0.7	22
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
0.8313	Intermediate Similarity	NPC31839
0.7791	Intermediate Similarity	NPC242611
0.7527	Intermediate Similarity	NPC488516
0.7263	Intermediate Similarity	NPC80843
0.7216	Intermediate Similarity	NPC180550
0.7216	Intermediate Similarity	NPC35405
0.7045	Intermediate Similarity	NPC606107
0.7	Intermediate Similarity	NPC488515
0.6628	Remote Similarity	NPC601365
0.6571	Remote Similarity	NPC475486
0.6531	Remote Similarity	NPC480424
0.65	Remote Similarity	NPC469945
0.6484	Remote Similarity	NPC283849
0.6458	Remote Similarity	NPC76999
0.6449	Remote Similarity	NPC288205
0.6449	Remote Similarity	NPC51465
0.6381	Remote Similarity	NPC75318
0.6374	Remote Similarity	NPC204407
0.6289	Remote Similarity	NPC164194
0.62	Remote Similarity	NPC127056
0.6186	Remote Similarity	NPC214484
0.617	Remote Similarity	NPC286347
0.6118	Remote Similarity	NPC228784
0.6118	Remote Similarity	NPC324341
0.6118	Remote Similarity	NPC601810
0.61	Remote Similarity	NPC25605
0.61	Remote Similarity	NPC56713
0.6055	Remote Similarity	NPC62725
0.604	Remote Similarity	NPC114441
0.604	Remote Similarity	NPC109079
0.598	Remote Similarity	NPC472949
0.5922	Remote Similarity	NPC22956
0.5909	Remote Similarity	NPC222047
0.5905	Remote Similarity	NPC104400
0.5905	Remote Similarity	NPC10320
0.5859	Remote Similarity	NPC480938
0.5842	Remote Similarity	NPC136877
0.5833	Remote Similarity	NPC37134
0.5825	Remote Similarity	NPC488561
0.581	Remote Similarity	NPC114304
0.58	Remote Similarity	NPC270667
0.5794	Remote Similarity	NPC257468
0.5789	Remote Similarity	NPC28198
0.5789	Remote Similarity	NPC476123
0.578	Remote Similarity	NPC291903
0.5773	Remote Similarity	NPC100383
0.5758	Remote Similarity	NPC480951
0.5741	Remote Similarity	NPC79718
0.57	Remote Similarity	NPC475472
0.5673	Remote Similarity	NPC6377
0.5673	Remote Similarity	NPC208381
0.5636	Remote Similarity	NPC324875
0.5636	Remote Similarity	NPC292677
0.5631	Remote Similarity	NPC59804
0.5596	Remote Similarity	NPC119794
0.5586	Remote Similarity	NPC488564
0.5575	Remote Similarity	NPC475119
0.5568	Remote Similarity	NPC120840
0.5566	Remote Similarity	NPC223301
0.5566	Remote Similarity	NPC171544
0.5534	Remote Similarity	NPC12288
0.5526	Remote Similarity	NPC473824
0.5524	Remote Similarity	NPC39211
0.5506	Remote Similarity	NPC201657
0.55	Remote Similarity	NPC294112
0.55	Remote Similarity	NPC284807
0.5481	Remote Similarity	NPC174679
0.5481	Remote Similarity	NPC279554
0.5463	Remote Similarity	NPC2370
0.5446	Remote Similarity	NPC191410
0.5444	Remote Similarity	NPC471588
0.5405	Remote Similarity	NPC145899
0.5392	Remote Similarity	NPC473481
0.5364	Remote Similarity	NPC481082
0.5364	Remote Similarity	NPC73829
0.5364	Remote Similarity	NPC164419
0.5351	Remote Similarity	NPC480939
0.534	Remote Similarity	NPC1046
0.5306	Remote Similarity	NPC57362
0.5283	Remote Similarity	NPC249848
0.5283	Remote Similarity	NPC107966
0.5273	Remote Similarity	NPC139044
0.5254	Remote Similarity	NPC166422
0.5254	Remote Similarity	NPC219180
0.5254	Remote Similarity	NPC251263
0.5234	Remote Similarity	NPC157868
0.5221	Remote Similarity	NPC323359
0.5217	Remote Similarity	NPC488521
0.5196	Remote Similarity	NPC475633
0.5189	Remote Similarity	NPC108748
0.5182	Remote Similarity	NPC40775
0.5182	Remote Similarity	NPC44716
0.5182	Remote Similarity	NPC10607
0.5182	Remote Similarity	NPC159309
0.5182	Remote Similarity	NPC473383
0.5182	Remote Similarity	NPC86222
0.5179	Remote Similarity	NPC64715
0.5175	Remote Similarity	NPC488209
0.5167	Remote Similarity	NPC54636
0.5161	Remote Similarity	NPC6255
0.5138	Remote Similarity	NPC192791
0.5135	Remote Similarity	NPC471383
0.5133	Remote Similarity	NPC281148
0.5133	Remote Similarity	NPC276093
0.5128	Remote Similarity	NPC200788
0.5096	Remote Similarity	NPC171007
0.5096	Remote Similarity	NPC190849
0.5091	Remote Similarity	NPC30735
0.5086	Remote Similarity	NPC280941
0.5086	Remote Similarity	NPC235772
0.5055	Remote Similarity	NPC200752
0.5048	Remote Similarity	NPC127853
0.5047	Remote Similarity	NPC235405
0.5045	Remote Similarity	NPC251768
0.5045	Remote Similarity	NPC488526
0.5042	Remote Similarity	NPC243680

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC274411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5985
0.1-0.2	3094
0.2-0.3	60
0.3-0.4	10
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