NPASS Compound

Natural Product: NPC143842

Natural Product ID	NPC143842
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OQZGLOBKVNEEPK-HYYJYYHTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	164965
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 102108 0 0 0 0 0 0 0 0999 V2000 -4.2115 -1.1748 1.4758 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4608 -1.5450 0.0374 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4952 -0.6293 -0.5771 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8693 0.3362 -1.5485 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4989 0.7646 -1.1817 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6931 -0.2609 -0.4720 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2679 -1.5070 -0.6637 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4159 -0.3696 -1.0594 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3881 -0.1189 -0.1123 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3609 -1.3883 0.0056 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7152 -1.1736 0.5736 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4640 -0.2602 -0.3976 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2001 -0.7488 -1.8036 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8325 1.1023 -0.2887 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2093 1.7244 1.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6952 1.8212 1.2374 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4690 1.1367 0.1369 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8926 -0.2512 0.0006 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6815 -1.0228 -1.0699 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0249 -1.2757 -0.4430 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7231 0.0262 -0.2183 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3537 0.5058 -1.5204 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8645 -0.2744 0.7466 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8241 0.8544 1.7611 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3143 1.1667 1.8617 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9212 1.1101 0.4090 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4289 2.3338 -0.1460 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1662 -0.4616 0.1119 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2256 0.3053 0.3445 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3513 -0.1568 -0.4510 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5207 0.3313 -0.4863 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9240 -1.2339 -1.1730 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6011 -1.5112 -0.8357 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3656 1.1012 -0.5105 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8525 1.2733 -2.3155 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6589 1.4807 -1.6800 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2012 -0.0238 0.4492 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5422 -0.3926 0.4588 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9633 -1.0609 1.7400 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4516 -0.8459 1.9093 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1630 -0.5875 0.6190 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5047 0.4208 -0.2678 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3249 1.6937 -0.3893 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6716 2.6391 -1.1682 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2918 0.7788 0.3280 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3993 -1.7472 -0.1104 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7341 0.1736 2.8091 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7731 -2.4527 1.5919 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9256 -1.7705 2.0981 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2072 -1.4693 1.8461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3207 -0.0870 1.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8202 -2.6003 0.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2027 -1.2663 -1.1409 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8198 -0.1178 -2.5834 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5947 1.6682 -0.5022 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6112 0.0112 0.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9269 0.0780 0.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1942 -2.0449 0.7352 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3976 -1.9859 -0.9305 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2834 -2.1089 0.7535 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6144 -0.6954 1.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8960 -0.2833 -2.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1890 -1.8545 -1.8841 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1825 -0.3523 -2.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2961 1.7445 -1.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8401 2.7922 0.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6614 1.3059 1.8967 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0568 2.8810 1.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9326 1.2531 2.1827 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2936 1.6328 -0.8493 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1046 -0.7912 0.9500 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1382 -1.9335 -1.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8528 -0.3899 -1.9706 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6772 -1.8825 -1.1113 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8845 -1.8271 0.5216 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4228 0.6685 -1.3905 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8598 1.4448 -1.8693 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1493 -0.2520 -2.2892 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6569 -1.2125 1.3410 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3906 1.7159 1.4085 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1812 0.5461 2.7640 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2510 2.1831 2.2830 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8138 0.3824 2.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9603 3.1024 0.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3147 1.1692 1.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5931 -2.5211 -0.2983 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0103 -1.5888 -1.7530 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0632 1.9666 0.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1566 1.3718 -1.5918 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5035 1.4612 -3.0626 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2113 1.4469 -2.4941 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7772 -1.1091 -0.3698 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3642 -0.7588 2.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9179 -1.7748 2.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1804 -0.1780 0.8893 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3149 0.0556 -1.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5689 2.1255 0.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2882 1.4379 -0.8752 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1872 2.2281 -1.9197 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2505 -1.5696 -1.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0427 0.8769 2.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0640 -2.5811 0.9083 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 23 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 14 34 1 0 5 35 1 0 4 36 1 0 3 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 40 47 1 0 39 48 1 0 7 2 1 0 34 9 1 0 45 38 1 0 18 12 1 0 26 21 1 0 33 28 1 0 26 17 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 1 3 53 1 0 4 54 1 6 5 55 1 1 6 56 1 0 9 57 1 1 10 58 1 0 10 59 1 0 11 60 1 0 11 61 1 0 13 62 1 0 13 63 1 0 13 64 1 0 14 65 1 6 15 66 1 0 15 67 1 0 16 68 1 0 16 69 1 0 17 70 1 6 18 71 1 1 19 72 1 0 19 73 1 0 20 74 1 0 20 75 1 0 22 76 1 0 22 77 1 0 22 78 1 0 23 79 1 1 24 80 1 0 24 81 1 0 25 82 1 0 25 83 1 0 27 84 1 0 29 85 1 0 33 86 1 0 33 87 1 0 34 88 1 0 34 89 1 0 35 90 1 0 36 91 1 0 38 92 1 6 39 93 1 1 40 94 1 1 41 95 1 1 42 96 1 6 43 97 1 0 43 98 1 0 44 99 1 0 46100 1 0 47101 1 0 48102 1 0 M END

Standard InCHIKey	OQZGLOBKVNEEPK-HYYJYYHTSA-N
Standard InCHI	InChI=1S/C35H54O13/c1-16-30(48-32-28(41)26(39)25(38)23(14-36)47-32)27(40)29(42)31(45-16)46-19-6-9-33(2)18(13-19)4-5-22-21(33)7-10-34(3)20(8-11-35(22,34)43)17-12-24(37)44-15-17/h12,16,18-23,25-32,36,38-43H,4-11,13-15H2,1-3H3/t16-,18+,19-,20+,21-,22+,23+,25+,26-,27-,28+,29-,30?,31?,32-,33-,34+,35-/m0/s1
SMILES	C[C@H]1C([C@H]([C@@H](C(O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	682.36	Volume:	663.021 ? Van der Waals volume.
Dense:	1.029	LogP:	0.84 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.653 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.144 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	38.0
TPSA:	204.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.149	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.53	Fsp³:	0.914
MCE-18:	133.284 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.71	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.021 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.114	Promiscuous compounds:	0.142

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.444	MDCK Permeability:	-5.188
Pgp-inhibitor:	0.001	Pgp-substrate:	0.867
PAMPA:	0.995 ? 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):	0.303
20% Bioavailability (F20%):	0.451	30% Bioavailability (F30%):	0.966
50% Bioavailability (F50%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.202
Plasma Protein Binding (PPB):	65.453%	Volume Distribution (VD):	-0.512
Fu:	32.767% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.046
BSEP inhibitor:	0.038

ADMET: Metabolism

CYP1A2-inhibitor:	0.078	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.013	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.232	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.015
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):

1.009

Half-life (T1/2):

3.593

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.249
Human Hepatotoxicity (H-HT):	0.749	Drug-induced Liver Injury (DILI):	0.96
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.801
Maximum Recommended Daily Dose:	0.997	Skin Sensitization:	1.0
Carcinogencity:	0.739	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.783
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.968
Hematotoxicity:	0.783	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.817
A549 Cytotoxicity:	0.624	Hek293 Cytotoxicity:	0.971
BCF:	0.542 ? 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:	3.131 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.45 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.64 ? 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
NPO28394	Rohdea chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28394	Rohdea chinensis	Species	Asparagaceae	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 NPC143842 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	14937
0.1-0.2	28917
0.2-0.3	4666
0.3-0.4	1059
0.4-0.5	118
0.5-0.6	54
0.6-0.7	62
0.7-0.8	1
0.8-0.85	6
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236973
0.8961	High Similarity	NPC5311
0.878	High Similarity	NPC32177
0.878	High Similarity	NPC469756
0.878	High Similarity	NPC275901
0.8675	High Similarity	NPC188234
0.8471	Intermediate Similarity	NPC486143
0.8471	Intermediate Similarity	NPC486142
0.8471	Intermediate Similarity	NPC486149
0.8214	Intermediate Similarity	NPC30483
0.8214	Intermediate Similarity	NPC470897
0.8	Intermediate Similarity	NPC99620
0.7935	Intermediate Similarity	NPC120390
0.7912	Intermediate Similarity	NPC486144
0.7912	Intermediate Similarity	NPC486145
0.7912	Intermediate Similarity	NPC486147
0.7912	Intermediate Similarity	NPC475590
0.7912	Intermediate Similarity	NPC486148
0.7907	Intermediate Similarity	NPC292467
0.7805	Intermediate Similarity	NPC77299
0.7805	Intermediate Similarity	NPC480906
0.7711	Intermediate Similarity	NPC480914
0.7701	Intermediate Similarity	NPC40749
0.7667	Intermediate Similarity	NPC486146
0.7614	Intermediate Similarity	NPC32793
0.7614	Intermediate Similarity	NPC116075
0.7558	Intermediate Similarity	NPC480907
0.7553	Intermediate Similarity	NPC74259
0.7444	Intermediate Similarity	NPC125077
0.7444	Intermediate Similarity	NPC486135
0.7444	Intermediate Similarity	NPC486137
0.7363	Intermediate Similarity	NPC232785
0.7363	Intermediate Similarity	NPC486139
0.7294	Intermediate Similarity	NPC76572
0.7294	Intermediate Similarity	NPC193382
0.7253	Intermediate Similarity	NPC208193
0.7245	Intermediate Similarity	NPC474423
0.7222	Intermediate Similarity	NPC240070
0.7188	Intermediate Similarity	NPC475419
0.7143	Intermediate Similarity	NPC231518
0.7143	Intermediate Similarity	NPC488944
0.7113	Intermediate Similarity	NPC474908
0.7113	Intermediate Similarity	NPC486134
0.7113	Intermediate Similarity	NPC486141
0.7033	Intermediate Similarity	NPC480910
0.7033	Intermediate Similarity	NPC480909
0.6979	Remote Similarity	NPC486136
0.6977	Remote Similarity	NPC469750
0.6966	Remote Similarity	NPC72260
0.6957	Remote Similarity	NPC264336
0.686	Remote Similarity	NPC84987
0.6771	Remote Similarity	NPC475219
0.6744	Remote Similarity	NPC471633
0.6737	Remote Similarity	NPC329986
0.6737	Remote Similarity	NPC140092
0.6702	Remote Similarity	NPC59288
0.6701	Remote Similarity	NPC479360
0.6701	Remote Similarity	NPC479359
0.6701	Remote Similarity	NPC488943
0.6701	Remote Similarity	NPC488942
0.6667	Remote Similarity	NPC475556
0.6667	Remote Similarity	NPC486138
0.6667	Remote Similarity	NPC276838
0.6667	Remote Similarity	NPC311706
0.6596	Remote Similarity	NPC475629
0.6517	Remote Similarity	NPC199428
0.6517	Remote Similarity	NPC109448
0.6517	Remote Similarity	NPC310341
0.6489	Remote Similarity	NPC479353
0.6489	Remote Similarity	NPC479354
0.6489	Remote Similarity	NPC486130
0.6477	Remote Similarity	NPC196429
0.6436	Remote Similarity	NPC117445
0.6436	Remote Similarity	NPC308262
0.6421	Remote Similarity	NPC488941
0.6421	Remote Similarity	NPC488940
0.6421	Remote Similarity	NPC486127
0.6354	Remote Similarity	NPC55532
0.6333	Remote Similarity	NPC84949
0.6333	Remote Similarity	NPC480562
0.6333	Remote Similarity	NPC74945
0.6333	Remote Similarity	NPC31354
0.6333	Remote Similarity	NPC69576
0.6311	Remote Similarity	NPC488945
0.6311	Remote Similarity	NPC488946
0.6222	Remote Similarity	NPC157376
0.6222	Remote Similarity	NPC142066
0.6222	Remote Similarity	NPC603972
0.6214	Remote Similarity	NPC486150
0.62	Remote Similarity	NPC488938
0.62	Remote Similarity	NPC488937
0.6196	Remote Similarity	NPC93883
0.6196	Remote Similarity	NPC471353
0.618	Remote Similarity	NPC99728
0.618	Remote Similarity	NPC87250
0.618	Remote Similarity	NPC244402
0.618	Remote Similarity	NPC50305
0.61	Remote Similarity	NPC479357
0.61	Remote Similarity	NPC486132
0.61	Remote Similarity	NPC486131
0.6044	Remote Similarity	NPC17896
0.6044	Remote Similarity	NPC469755
0.6044	Remote Similarity	NPC284406
0.6044	Remote Similarity	NPC197707
0.6044	Remote Similarity	NPC251866
0.6044	Remote Similarity	NPC480915
0.604	Remote Similarity	NPC486128
0.6022	Remote Similarity	NPC484202
0.5981	Remote Similarity	NPC286809
0.596	Remote Similarity	NPC469749
0.59	Remote Similarity	NPC146857
0.59	Remote Similarity	NPC488939
0.5851	Remote Similarity	NPC179412
0.5851	Remote Similarity	NPC471356
0.5851	Remote Similarity	NPC305574
0.5833	Remote Similarity	NPC173555
0.581	Remote Similarity	NPC486140
0.581	Remote Similarity	NPC329675
0.5806	Remote Similarity	NPC243196
0.5794	Remote Similarity	NPC488947
0.5789	Remote Similarity	NPC193893
0.5784	Remote Similarity	NPC476221
0.5784	Remote Similarity	NPC477709
0.5758	Remote Similarity	NPC610296
0.5755	Remote Similarity	NPC486133
0.5743	Remote Similarity	NPC247190
0.5684	Remote Similarity	NPC483822
0.5579	Remote Similarity	NPC146456
0.5579	Remote Similarity	NPC250556
0.5543	Remote Similarity	NPC158344
0.5514	Remote Similarity	NPC194716
0.5495	Remote Similarity	NPC486152
0.5476	Remote Similarity	NPC268829
0.5476	Remote Similarity	NPC295110
0.5426	Remote Similarity	NPC219085
0.5426	Remote Similarity	NPC309034
0.54	Remote Similarity	NPC27363
0.5377	Remote Similarity	NPC479358
0.5368	Remote Similarity	NPC479356
0.5368	Remote Similarity	NPC479355
0.5347	Remote Similarity	NPC608063
0.5321	Remote Similarity	NPC329784
0.5319	Remote Similarity	NPC473852
0.5258	Remote Similarity	NPC77319
0.5258	Remote Similarity	NPC471351
0.5258	Remote Similarity	NPC471355
0.5208	Remote Similarity	NPC99080
0.5172	Remote Similarity	NPC222875
0.5172	Remote Similarity	NPC25177
0.5152	Remote Similarity	NPC471354
0.5152	Remote Similarity	NPC27507
0.5057	Remote Similarity	NPC480913
0.5053	Remote Similarity	NPC474418
0.5051	Remote Similarity	NPC9499
0.5051	Remote Similarity	NPC471360
0.5051	Remote Similarity	NPC469751
0.5051	Remote Similarity	NPC471361
0.5051	Remote Similarity	NPC86159
0.5051	Remote Similarity	NPC469752
0.5051	Remote Similarity	NPC469754
0.5051	Remote Similarity	NPC70542
0.505	Remote Similarity	NPC5883

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC143842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6109
0.1-0.2	2908
0.2-0.3	107
0.3-0.4	9
0.4-0.5	7
0.5-0.6	6
0.6-0.7	3
0.7-0.8	1
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
0.7143	Intermediate Similarity	NPD8033	Approved
0.6966	Remote Similarity	NPD8294	Phase 4
0.6354	Remote Similarity	NPD8377	Phase 4
0.6044	Remote Similarity	NPD7319	Approved
0.5833	Remote Similarity	NPD8296	Phase 4
0.5745	Remote Similarity	NPD8335	Phase 4
0.5684	Remote Similarity	NPD8380	Approved
0.5579	Remote Similarity	NPD7507	Pre-clinical
0.534	Remote Similarity	NPD8378	Pre-clinical
0.534	Remote Similarity	NPD8379	Approved

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