NPASS Compound

Natural Product: NPC476123

Natural Product ID	NPC476123
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-[(Alpha-L-Arabinopyranosyl)Oxy]-23-Hydroxyolean-12-En-28-Oic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL538200
PubChem CID	25087737
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 2.9247 -0.9926 -2.4019 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5071 0.2061 -2.0265 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1411 0.4697 -0.5528 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8108 1.7912 -0.2163 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7770 -0.6279 0.2293 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0891 -0.9348 1.5307 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6018 -0.9448 1.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0366 0.3532 0.8538 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6614 0.5166 -0.4998 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1132 1.7473 -1.1431 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3508 1.4383 -1.4888 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1312 1.0405 -0.2665 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4285 0.0610 0.6143 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2233 -0.2107 1.8375 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6588 -0.1254 1.5728 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2527 0.1159 0.4124 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 0.3289 -0.7759 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0492 -1.0719 -1.2950 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0356 1.0588 -1.8990 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4473 0.6454 -2.1110 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3123 0.7227 -0.8877 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7398 0.1594 0.3442 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2322 -1.2522 0.6353 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7329 -1.2700 0.8581 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4390 -0.3484 -0.0819 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6281 0.0350 -1.2887 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0543 -0.9152 2.2930 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1868 -2.6988 0.6304 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6695 2.1494 -0.6842 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3277 2.6972 0.3914 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3570 2.8975 -1.6190 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5991 2.2787 0.4472 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3239 1.4362 1.8204 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0797 -0.2724 0.5258 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0314 -1.1716 0.0582 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6067 -1.7318 1.2258 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2547 -0.6732 1.9026 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6373 -0.5767 1.2934 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5036 -0.9611 -0.1648 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1431 -0.5486 -0.7185 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1441 -1.0311 -2.0486 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5241 -0.4604 -0.9471 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1962 0.6885 1.4475 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4753 -1.4725 -3.0898 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2729 1.0491 -2.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6114 0.0267 -2.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2391 2.6624 -0.5378 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7992 1.8377 -0.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1001 1.8345 0.8661 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7889 -1.5939 -0.3465 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3886 -1.9796 1.8354 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5165 -0.2785 2.2986 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2701 -1.8263 0.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2109 -0.9658 2.4963 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2839 -0.3545 -1.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0810 2.6389 -0.5064 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5941 2.0342 -2.0923 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7665 2.4272 -1.8354 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4226 0.7508 -2.3299 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4093 -0.9128 0.0324 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9687 0.4136 2.7162 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0153 -1.2702 2.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3222 -0.2809 2.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8653 -1.3499 -2.0264 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1425 -1.8363 -0.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1231 -1.1047 -1.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4750 0.7625 -2.8369 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9644 2.1530 -1.8645 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5508 -0.3575 -2.5962 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8902 1.3573 -2.8699 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0578 0.7648 1.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0071 -1.8752 -0.2457 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7706 -1.6190 1.5748 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8492 0.5297 0.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3469 -0.8800 -0.4935 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1982 0.7430 -1.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3861 -0.8419 -1.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6631 -1.6969 2.7974 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1234 -0.8101 2.9038 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6717 0.0237 2.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2414 -2.7581 0.3118 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9894 -3.3321 1.5373 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5739 -3.1257 -0.2019 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5491 3.8656 -1.3994 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5999 2.6356 0.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8998 3.1026 0.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7347 2.1542 1.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0725 1.1230 2.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4694 1.8182 2.3957 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8086 2.3472 1.3679 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6008 -2.0295 -0.4816 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2598 -0.8261 2.9814 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6694 0.2634 1.6954 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2661 -1.3254 1.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4851 -2.0894 -0.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0207 0.5614 -0.6969 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9097 -0.2609 -2.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6817 -1.1452 -1.6704 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8416 0.9054 0.7293 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 3 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 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 24 28 1 0 21 29 1 1 29 30 2 0 29 31 1 0 12 32 1 1 8 33 1 1 5 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 9 3 1 0 17 12 1 0 26 21 1 0 40 35 1 0 13 8 1 0 22 16 1 0 1 44 1 0 2 45 1 0 2 46 1 0 4 47 1 0 4 48 1 0 4 49 1 0 5 50 1 6 6 51 1 0 6 52 1 0 7 53 1 0 7 54 1 0 9 55 1 6 10 56 1 0 10 57 1 0 11 58 1 0 11 59 1 0 13 60 1 6 14 61 1 0 14 62 1 0 15 63 1 0 18 64 1 0 18 65 1 0 18 66 1 0 19 67 1 0 19 68 1 0 20 69 1 0 20 70 1 0 22 71 1 1 23 72 1 0 23 73 1 0 25 74 1 0 25 75 1 0 26 76 1 0 26 77 1 0 27 78 1 0 27 79 1 0 27 80 1 0 28 81 1 0 28 82 1 0 28 83 1 0 31 84 1 0 32 85 1 0 32 86 1 0 32 87 1 0 33 88 1 0 33 89 1 0 33 90 1 0 35 91 1 6 37 92 1 0 37 93 1 0 38 94 1 1 39 95 1 1 40 96 1 6 41 97 1 0 42 98 1 0 43 99 1 0 M END

Standard InCHIKey	QUBNLZCADIYAFW-DRHKFHIJSA-N
Standard InCHI	InChI=1S/C35H56O8/c1-30(2)13-15-35(29(40)41)16-14-33(5)20(21(35)17-30)7-8-24-31(3)11-10-25(43-28-27(39)26(38)22(37)18-42-28)32(4,19-36)23(31)9-12-34(24,33)6/h7,21-28,36-39H,8-19H2,1-6H3,(H,40,41)/t21-,22-,23+,24+,25-,26-,27+,28-,31-,32?,33+,34+,35-/m0/s1
SMILES	OCC1(C)[C@H](CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	604.4	Volume:	627.626 ? Van der Waals volume.
Dense:	0.963	LogP:	3.199 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.09 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.986 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	136.68 ? 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:	0.231	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.269	Fsp³:	0.914
MCE-18:	126.328 ? 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:	0.971	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.189	Promiscuous compounds:	0.082

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.904	MDCK Permeability:	-5.199
Pgp-inhibitor:	0.0	Pgp-substrate:	0.023
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):	0.03
20% Bioavailability (F20%):	0.529	30% Bioavailability (F30%):	0.231
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136	MRP1:	0.967
Plasma Protein Binding (PPB):	79.824%	Volume Distribution (VD):	-0.527
Fu:	14.273% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.754	BCRP inhibitor:	0.003
BSEP inhibitor:	0.067

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.794	CYP3A4-substrate:	0.441
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.006
HLM stability:	0.044 ? 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):

0.894

Half-life (T1/2):

1.538

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.02
Human Hepatotoxicity (H-HT):	0.798	Drug-induced Liver Injury (DILI):	0.83
AMES Toxicity:	0.623	Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.066	Skin Sensitization:	0.998
Carcinogencity:	0.798	Eye Corrosion:	0.001
Eye Irritation:	0.274	Respiratory Toxicity:	0.614
Drug-induced Neurotoxicity:	0.023	Ototoxicity:	0.869
Hematotoxicity:	0.725	Drug-induced Nephrotoxicity:	0.959
Genotoxicity:	0.591	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.315	Hek293 Cytotoxicity:	0.162
BCF:	1.372 ? 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:	3.873 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.541 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.717 ? 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
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	underground parts	n.a.	n.a.	PMID[19449879]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	12.5	ug.mL-1	PMID[20585113]

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 NPC476123 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	18673
0.1-0.2	25657
0.2-0.3	4142
0.3-0.4	867
0.4-0.5	361
0.5-0.6	81
0.6-0.7	46
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC28198
0.8933	High Similarity	NPC283849
0.859	High Similarity	NPC100383
0.8077	Intermediate Similarity	NPC204407
0.7875	Intermediate Similarity	NPC177246
0.7711	Intermediate Similarity	NPC284807
0.7674	Intermediate Similarity	NPC136877
0.7614	Intermediate Similarity	NPC6377
0.7614	Intermediate Similarity	NPC488561
0.7614	Intermediate Similarity	NPC208381
0.7586	Intermediate Similarity	NPC174679
0.7586	Intermediate Similarity	NPC279554
0.7586	Intermediate Similarity	NPC59804
0.7317	Intermediate Similarity	NPC606107
0.7283	Intermediate Similarity	NPC104400
0.7283	Intermediate Similarity	NPC10320
0.7262	Intermediate Similarity	NPC242611
0.7253	Intermediate Similarity	NPC469945
0.7241	Intermediate Similarity	NPC270667
0.7053	Intermediate Similarity	NPC79718
0.7045	Intermediate Similarity	NPC127853
0.6947	Remote Similarity	NPC481082
0.6947	Remote Similarity	NPC164419
0.6941	Remote Similarity	NPC286347
0.6931	Remote Similarity	NPC323341
0.6923	Remote Similarity	NPC127056
0.6897	Remote Similarity	NPC473538
0.6889	Remote Similarity	NPC12288
0.6813	Remote Similarity	NPC56713
0.6804	Remote Similarity	NPC276093
0.6771	Remote Similarity	NPC73829
0.6705	Remote Similarity	NPC294112
0.6667	Remote Similarity	NPC139044
0.6667	Remote Similarity	NPC471383
0.6535	Remote Similarity	NPC280941
0.6535	Remote Similarity	NPC235772
0.65	Remote Similarity	NPC488209
0.6484	Remote Similarity	NPC164194
0.6422	Remote Similarity	NPC471385
0.6381	Remote Similarity	NPC166422
0.6364	Remote Similarity	NPC480946
0.6364	Remote Similarity	NPC130577
0.6364	Remote Similarity	NPC142415
0.6364	Remote Similarity	NPC102683
0.6329	Remote Similarity	NPC120840
0.6322	Remote Similarity	NPC57362
0.6316	Remote Similarity	NPC472949
0.6316	Remote Similarity	NPC488516
0.6286	Remote Similarity	NPC133818
0.6282	Remote Similarity	NPC270768
0.6282	Remote Similarity	NPC59263
0.6282	Remote Similarity	NPC210106
0.6277	Remote Similarity	NPC25605
0.625	Remote Similarity	NPC22956
0.6238	Remote Similarity	NPC324875
0.6238	Remote Similarity	NPC292677
0.6224	Remote Similarity	NPC180550
0.6224	Remote Similarity	NPC35405
0.6211	Remote Similarity	NPC114441
0.6211	Remote Similarity	NPC109079
0.62	Remote Similarity	NPC119794
0.61	Remote Similarity	NPC257468
0.604	Remote Similarity	NPC488515
0.6024	Remote Similarity	NPC96580
0.6	Remote Similarity	NPC31839
0.6	Remote Similarity	NPC158141
0.6	Remote Similarity	NPC110308
0.596	Remote Similarity	NPC114304
0.5957	Remote Similarity	NPC22676
0.5926	Remote Similarity	NPC219180
0.5926	Remote Similarity	NPC298554
0.5922	Remote Similarity	NPC323359
0.5914	Remote Similarity	NPC191410
0.5876	Remote Similarity	NPC480424
0.5875	Remote Similarity	NPC275809
0.5865	Remote Similarity	NPC488564
0.5851	Remote Similarity	NPC475472
0.5851	Remote Similarity	NPC475611
0.5802	Remote Similarity	NPC231063
0.5802	Remote Similarity	NPC282395
0.578	Remote Similarity	NPC251263
0.5758	Remote Similarity	NPC80843
0.5755	Remote Similarity	NPC62725
0.5732	Remote Similarity	NPC200752
0.5701	Remote Similarity	NPC288205
0.5701	Remote Similarity	NPC51465
0.5699	Remote Similarity	NPC256798
0.5679	Remote Similarity	NPC182797
0.5679	Remote Similarity	NPC282616
0.5679	Remote Similarity	NPC84319
0.5679	Remote Similarity	NPC52021
0.5679	Remote Similarity	NPC52169
0.5679	Remote Similarity	NPC488562
0.5679	Remote Similarity	NPC599947
0.5657	Remote Similarity	NPC295371
0.5641	Remote Similarity	NPC604575
0.5619	Remote Similarity	NPC75318
0.561	Remote Similarity	NPC481360
0.5588	Remote Similarity	NPC473383
0.5581	Remote Similarity	NPC474727
0.5565	Remote Similarity	NPC161717
0.5556	Remote Similarity	NPC198664
0.5529	Remote Similarity	NPC296164
0.5521	Remote Similarity	NPC189884
0.5521	Remote Similarity	NPC138334
0.5521	Remote Similarity	NPC480938
0.5488	Remote Similarity	NPC121798
0.5488	Remote Similarity	NPC234346
0.5484	Remote Similarity	NPC224121
0.5422	Remote Similarity	NPC106112
0.5422	Remote Similarity	NPC261935
0.5398	Remote Similarity	NPC54636
0.5327	Remote Similarity	NPC477191
0.5312	Remote Similarity	NPC475633
0.5301	Remote Similarity	NPC37038
0.5301	Remote Similarity	NPC156981
0.5294	Remote Similarity	NPC474963
0.5283	Remote Similarity	NPC484832
0.5278	Remote Similarity	NPC477192
0.5273	Remote Similarity	NPC476992
0.5268	Remote Similarity	NPC471384
0.5248	Remote Similarity	NPC482748
0.5238	Remote Similarity	NPC130278
0.5234	Remote Similarity	NPC37134
0.5229	Remote Similarity	NPC475486
0.5204	Remote Similarity	NPC90856
0.5204	Remote Similarity	NPC171007
0.5204	Remote Similarity	NPC190849
0.5196	Remote Similarity	NPC473884
0.5185	Remote Similarity	NPC218954
0.5169	Remote Similarity	NPC601365
0.5138	Remote Similarity	NPC241909
0.5122	Remote Similarity	NPC280654
0.5119	Remote Similarity	NPC307282
0.5119	Remote Similarity	NPC64872
0.5119	Remote Similarity	NPC25906
0.5102	Remote Similarity	NPC195132
0.51	Remote Similarity	NPC198621
0.51	Remote Similarity	NPC216940
0.5059	Remote Similarity	NPC472149
0.5059	Remote Similarity	NPC609452
0.5057	Remote Similarity	NPC130520
0.5057	Remote Similarity	NPC608622
0.5052	Remote Similarity	NPC128925
0.505	Remote Similarity	NPC605663
0.5046	Remote Similarity	NPC301449
0.5046	Remote Similarity	NPC291903
0.5046	Remote Similarity	NPC601290

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5993
0.1-0.2	3080
0.2-0.3	66
0.3-0.4	9
0.4-0.5	1
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
0.5149	Remote Similarity	NPD8295	Clinical (unspecified phase)

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