NPASS Compound

Natural Product: NPC127683

Natural Product ID	NPC127683
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FKTQBZHKUPHHSC-SDUJRMPFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101756120
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 99104 0 0 0 0 0 0 0 0999 V2000 -5.3009 3.3743 0.4865 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0376 2.6342 -0.2761 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0683 3.3190 -1.1469 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9833 1.1653 -0.4134 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3257 0.6826 0.1992 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9207 -0.2066 1.3449 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6542 -0.8466 0.7533 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8422 -1.5764 1.7848 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4797 -1.8638 1.2365 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8131 -0.6610 0.6166 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5153 0.2816 1.7741 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6925 0.0645 -0.3618 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9984 1.2540 -0.9355 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6219 0.9201 -1.4861 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8121 0.1484 -0.4777 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6240 -0.0200 -0.8691 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8646 -0.4258 -2.2763 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2857 1.3293 -0.6529 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7636 1.3241 -0.8058 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5082 0.2291 -0.1385 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7520 -1.0544 0.0569 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2517 -2.1299 -0.8843 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1842 -1.5649 1.4525 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2793 -0.9207 0.1516 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5967 -2.2477 0.2799 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7790 -2.0035 0.8198 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5541 -1.0818 -0.0979 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9193 -1.9337 -1.2968 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6228 -0.0828 -0.9473 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9685 0.1102 -0.5024 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0037 0.5716 0.6486 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0360 -0.2370 -1.3984 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2866 -0.0824 -1.1874 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8922 0.4902 -0.0216 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1271 -0.0511 0.4104 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8646 0.4783 1.4288 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4456 1.5926 2.1120 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2575 2.1500 1.7259 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5023 1.5958 0.6696 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1904 2.1446 3.1587 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9539 0.4441 0.3486 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1149 -1.7113 -0.3556 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1238 -2.4287 -1.0182 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3974 4.4574 0.5196 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5576 2.9584 1.1393 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8779 4.3877 -1.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0923 3.1559 -0.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0979 2.8714 -2.1579 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9891 0.9552 -1.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9394 1.5468 0.5424 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9201 0.1945 -0.5811 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6552 0.4575 2.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6654 -0.9632 1.5974 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3504 -2.5777 1.9205 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8793 -1.0991 2.7614 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8365 -2.1273 2.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5152 -2.7599 0.6329 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1900 0.0067 2.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7350 1.3285 1.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4926 0.1241 2.2022 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0052 -0.5496 -1.2317 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6049 1.6216 -1.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8881 2.1016 -0.2401 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7577 0.4442 -2.4539 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1098 1.8877 -1.6475 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7981 0.8161 0.4369 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7407 0.1329 -2.6691 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2228 -1.4864 -2.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0155 -0.3291 -2.9690 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8716 2.1219 -1.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0696 1.5892 0.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0810 1.4294 -1.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1092 2.3166 -0.3785 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8972 0.6266 0.8356 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5875 -2.9878 -0.9971 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2195 -2.5785 -0.4980 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5658 -1.6667 -1.8515 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5293 -1.1428 2.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1409 -2.6785 1.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2507 -1.3087 1.6106 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0822 -0.3996 1.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6033 -2.8611 -0.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1529 -2.8322 1.0437 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3240 -2.9931 0.7893 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7411 -1.7032 1.8603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4573 -1.4241 -2.0878 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4392 -2.8669 -1.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9673 -2.3073 -1.8031 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7839 -0.6942 -2.3990 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0137 -0.4298 -2.0014 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4771 -0.9399 -0.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8061 0.0330 1.7290 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9048 3.0262 2.2458 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6325 2.1527 0.3936 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3731 3.1537 3.2116 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7238 0.9800 1.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8574 -2.4823 -0.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6598 -1.1705 -1.1597 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4022 -2.6912 -1.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 8 9 1 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 20 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 12 41 1 0 7 42 1 6 42 43 1 0 41 4 1 0 41 7 1 0 27 10 1 0 39 34 1 0 27 15 1 0 24 16 1 0 1 44 1 0 1 45 1 0 3 46 1 0 3 47 1 0 3 48 1 0 4 49 1 6 5 50 1 0 5 51 1 0 6 52 1 0 6 53 1 0 8 54 1 0 8 55 1 0 9 56 1 0 9 57 1 0 11 58 1 0 11 59 1 0 11 60 1 0 12 61 1 6 13 62 1 0 13 63 1 0 14 64 1 0 14 65 1 0 15 66 1 1 17 67 1 0 17 68 1 0 17 69 1 0 18 70 1 0 18 71 1 0 19 72 1 0 19 73 1 0 20 74 1 1 22 75 1 0 22 76 1 0 22 77 1 0 23 78 1 0 23 79 1 0 23 80 1 0 24 81 1 1 25 82 1 0 25 83 1 0 26 84 1 0 26 85 1 0 28 86 1 0 28 87 1 0 28 88 1 0 32 89 1 0 33 90 1 0 35 91 1 0 36 92 1 0 38 93 1 0 39 94 1 0 40 95 1 0 41 96 1 1 42 97 1 0 42 98 1 0 43 99 1 0 M END

Standard InCHIKey	FKTQBZHKUPHHSC-SDUJRMPFSA-N
Standard InCHI	InChI=1S/C39H56O4/c1-25(2)28-16-21-39(24-40)23-22-37(6)29(34(28)39)13-14-31-36(5)19-18-32(35(3,4)30(36)17-20-38(31,37)7)43-33(42)15-10-26-8-11-27(41)12-9-26/h8-12,15,28-32,34,40-41H,1,13-14,16-24H2,2-7H3/b15-10-/t28-,29+,30-,31+,32-,34+,36-,37+,38+,39+/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)/C=Cc3ccc(cc3)O)[C@@H]12)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	588.42	Volume:	651.103 ? Van der Waals volume.
Dense:	0.904	LogP:	6.758 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.184 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.179 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	34.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.205	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.895	Fsp³:	0.718
MCE-18:	155.955 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.993	Fluc inhibitor:	0.976 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.166	Promiscuous compounds:	0.166

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.53	MDCK Permeability:	-5.081
Pgp-inhibitor:	0.36	Pgp-substrate:	0.028
PAMPA:	0.048 ? 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):	0.0
20% Bioavailability (F20%):	0.871	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332	MRP1:	0.798
Plasma Protein Binding (PPB):	97.698%	Volume Distribution (VD):	0.162
Fu:	2.075% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.845	BCRP inhibitor:	0.026
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.98	CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.051	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.233	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.03 ? 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):

7.477

Half-life (T1/2):

0.941

ADMET: Toxicity

hERG Blockers:	0.407	hERG Blockers (10um):	0.595
Human Hepatotoxicity (H-HT):	0.749	Drug-induced Liver Injury (DILI):	0.159
AMES Toxicity:	0.307	Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.748	Skin Sensitization:	1.0
Carcinogencity:	0.39	Eye Corrosion:	0.021
Eye Irritation:	0.813	Respiratory Toxicity:	0.882
Drug-induced Neurotoxicity:	0.326	Ototoxicity:	0.225
Hematotoxicity:	0.081	Drug-induced Nephrotoxicity:	0.866
Genotoxicity:	0.395	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.885	Hek293 Cytotoxicity:	0.895
BCF:	1.59 ? 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:	4.83 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.097 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.61 ? 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
NPO26828	Barbarea verna	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25482	Phyllogeiton zeyheri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23780	Psoroma crassum	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26183	Scabiosa pyrenaica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26828	Barbarea verna	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25482	Phyllogeiton zeyheri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2201	Orthocaulis attenuatus	Species	Anastrophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25532	Blitum virgatum	Species	Chenopodiaceae	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 NPC127683 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	7385
0.1-0.2	36983
0.2-0.3	4986
0.3-0.4	400
0.4-0.5	72
0.5-0.6	16
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8933	High Similarity	NPC148404
0.8933	High Similarity	NPC35212
0.8919	High Similarity	NPC478273
0.7975	Intermediate Similarity	NPC310621
0.7625	Intermediate Similarity	NPC11266
0.7412	Intermediate Similarity	NPC478274
0.7262	Intermediate Similarity	NPC252133
0.7024	Intermediate Similarity	NPC478270
0.7024	Intermediate Similarity	NPC478271
0.6944	Remote Similarity	NPC5280
0.686	Remote Similarity	NPC248287
0.686	Remote Similarity	NPC234548
0.6533	Remote Similarity	NPC168231
0.6429	Remote Similarity	NPC473612
0.6154	Remote Similarity	NPC8102
0.6154	Remote Similarity	NPC66894
0.5895	Remote Similarity	NPC478272
0.5833	Remote Similarity	NPC205392
0.5833	Remote Similarity	NPC105942
0.5684	Remote Similarity	NPC101863
0.5591	Remote Similarity	NPC182249
0.5513	Remote Similarity	NPC61107
0.5325	Remote Similarity	NPC305835
0.5281	Remote Similarity	NPC86257
0.5258	Remote Similarity	NPC486700
0.5258	Remote Similarity	NPC275312
0.5185	Remote Similarity	NPC304194
0.5155	Remote Similarity	NPC477874
0.5125	Remote Similarity	NPC98270
0.5104	Remote Similarity	NPC473591
0.51	Remote Similarity	NPC172311
0.5062	Remote Similarity	NPC611062

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC127683 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3837
0.1-0.2	5230
0.2-0.3	79
0.3-0.4	2
0.4-0.5	2
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