NPASS Compound

Natural Product: NPC100383

Natural Product ID	NPC100383
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-[(Alpha-Larabinopyranosyl)Oxy]-23-Oxo-Olean-12-En-28-Oic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-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	CHEMBL540458
PubChem CID	44179589
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 97102 0 0 0 0 0 0 0 0999 V2000 4.4470 -1.9128 0.8684 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6876 -1.9948 -0.0739 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1740 -0.7875 -0.8338 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6142 -1.0219 -2.2695 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8274 0.3953 -0.2221 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0395 1.6456 -0.1023 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 1.4192 0.2043 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9792 0.4856 -0.8695 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6967 -0.8154 -0.6639 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0235 -1.9561 -1.3977 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3208 -2.1492 -0.6818 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1347 -0.9128 -0.9738 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4657 0.3525 -0.6060 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2899 1.4911 -1.2229 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6703 1.3762 -0.7185 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1904 0.2549 -0.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3964 -1.0186 -0.1112 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0987 -1.4237 1.2929 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3480 -2.0720 -0.6986 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4581 -2.1955 0.3358 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2818 -0.9464 0.4650 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5961 0.3311 0.2361 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6473 1.3057 1.3960 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0335 1.4767 1.9516 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7804 0.1925 2.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9182 -1.0203 1.8629 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8754 2.2084 3.2917 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8862 2.4008 1.0875 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4486 -1.1328 -0.4741 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5717 -0.2912 -1.3922 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3406 -2.1688 -0.3426 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6115 -1.0155 -2.3963 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2597 1.1723 -2.1650 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0089 0.7420 -0.9267 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1402 0.6695 -0.1540 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7766 1.9320 -0.0468 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6632 1.8330 1.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2872 0.4859 1.1685 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4620 -0.2275 -0.1537 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1537 -0.1999 -0.8878 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6728 -1.4378 -1.2297 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4820 0.4413 -0.8378 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5308 0.6115 1.8276 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3733 -2.9826 -0.3721 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2348 -1.9332 -2.3973 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3037 -0.1726 -2.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7690 -1.1277 -2.9665 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1910 0.1395 0.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1396 2.3288 -0.9977 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4468 2.2463 0.7386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0529 2.3859 0.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4442 1.0184 1.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5270 -1.0631 0.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9053 -1.7864 -2.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5747 -2.8752 -1.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8286 -3.0101 -1.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0752 -2.2681 0.3900 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6251 0.5007 0.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2212 1.4617 -2.3312 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8626 2.4304 -0.8147 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2785 2.2978 -0.7806 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0395 -2.5511 1.3629 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8603 -1.0224 1.9822 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1176 -1.0811 1.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8596 -1.6695 -1.6156 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8790 -3.0392 -0.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0772 -2.5205 1.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0877 -3.0636 -0.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1411 0.8712 -0.5983 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3637 2.3064 0.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9472 1.0973 2.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7161 0.1633 1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1053 0.1275 3.1804 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6046 -1.8948 1.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1637 -1.1367 2.6389 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9332 1.8071 3.7550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6992 3.2774 3.0836 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7361 1.9961 3.9258 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5303 3.4522 1.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9923 2.0470 0.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9003 2.3913 1.5595 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2630 -2.0823 -0.7721 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0624 -2.0498 -2.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8358 -0.9825 -3.1554 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4341 -0.3090 -2.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3200 1.1695 -2.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0117 2.2652 -2.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6726 0.8636 -3.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9767 0.3564 0.8865 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0649 2.0424 1.9414 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4701 2.6016 0.9522 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6954 -0.2068 1.8279 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8172 -1.2514 0.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3500 0.3467 -1.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1949 -2.1148 -0.7406 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1904 1.3503 -1.1228 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3749 0.5863 2.8101 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 6 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 1 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 6 29 30 2 0 29 31 1 0 12 32 1 6 8 33 1 6 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 2 44 1 0 4 45 1 0 4 46 1 0 4 47 1 0 5 48 1 1 6 49 1 0 6 50 1 0 7 51 1 0 7 52 1 0 9 53 1 1 10 54 1 0 10 55 1 0 11 56 1 0 11 57 1 0 13 58 1 1 14 59 1 0 14 60 1 0 15 61 1 0 18 62 1 0 18 63 1 0 18 64 1 0 19 65 1 0 19 66 1 0 20 67 1 0 20 68 1 0 22 69 1 6 23 70 1 0 23 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 27 76 1 0 27 77 1 0 27 78 1 0 28 79 1 0 28 80 1 0 28 81 1 0 31 82 1 0 32 83 1 0 32 84 1 0 32 85 1 0 33 86 1 0 33 87 1 0 33 88 1 0 35 89 1 1 37 90 1 0 37 91 1 0 38 92 1 1 39 93 1 1 40 94 1 6 41 95 1 0 42 96 1 0 43 97 1 0 M END

Standard InCHIKey	QNJNYLJSUQIOBL-RITZIESXSA-N
Standard InCHI	InChI=1S/C35H54O8/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/h7,19,21-28,37-39H,8-18H2,1-6H3,(H,40,41)/t21-,22-,23+,24+,25-,26-,27+,28-,31-,32-,33+,34+,35-/m0/s1
SMILES	O=C[C@]1(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:	602.38	Volume:	624.99 ? Van der Waals volume.
Dense:	0.964	LogP:	2.933 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.019 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.872 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	34.0
TPSA:	133.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.203	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.339	Fsp³:	0.886
MCE-18:	126.848 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.96	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.177	Promiscuous compounds:	0.04

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.706	MDCK Permeability:	-5.193
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
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):	0.001
20% Bioavailability (F20%):	0.071	30% Bioavailability (F30%):	0.013
50% Bioavailability (F50%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077	MRP1:	0.803
Plasma Protein Binding (PPB):	84.497%	Volume Distribution (VD):	-0.534
Fu:	12.791% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.524	BCRP inhibitor:	0.012
BSEP inhibitor:	0.742

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.012	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.123	CYP3A4-substrate:	0.025
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.163 ? 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):

0.881

Half-life (T1/2):

1.494

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	0.81	Drug-induced Liver Injury (DILI):	0.868
AMES Toxicity:	0.86	Rat Oral Acute Toxicity:	0.277
Maximum Recommended Daily Dose:	0.181	Skin Sensitization:	1.0
Carcinogencity:	0.888	Eye Corrosion:	0.0
Eye Irritation:	0.055	Respiratory Toxicity:	0.664
Drug-induced Neurotoxicity:	0.032	Ototoxicity:	0.855
Hematotoxicity:	0.884	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.105
A549 Cytotoxicity:	0.512	Hek293 Cytotoxicity:	0.292
BCF:	0.932 ? 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:	3.834 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.474 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.692 ? 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	=	4.8	ug.mL-1	PMID[20545334]

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 NPC100383 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	17219
0.1-0.2	27091
0.2-0.3	4253
0.3-0.4	857
0.4-0.5	307
0.5-0.6	79
0.6-0.7	35
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
0.859	High Similarity	NPC283849
0.859	High Similarity	NPC28198
0.859	High Similarity	NPC476123
0.7857	Intermediate Similarity	NPC294112
0.7363	Intermediate Similarity	NPC6377
0.7363	Intermediate Similarity	NPC208381
0.7204	Intermediate Similarity	NPC469945
0.7174	Intermediate Similarity	NPC488561
0.7053	Intermediate Similarity	NPC104400
0.7053	Intermediate Similarity	NPC10320
0.7011	Intermediate Similarity	NPC242611
0.6941	Remote Similarity	NPC204407
0.686	Remote Similarity	NPC606107
0.6854	Remote Similarity	NPC284807
0.6782	Remote Similarity	NPC177246
0.6735	Remote Similarity	NPC481082
0.6735	Remote Similarity	NPC164419
0.6705	Remote Similarity	NPC286347
0.67	Remote Similarity	NPC323359
0.6667	Remote Similarity	NPC79718
0.6667	Remote Similarity	NPC136877
0.6596	Remote Similarity	NPC174679
0.6596	Remote Similarity	NPC279554
0.6596	Remote Similarity	NPC56713
0.6596	Remote Similarity	NPC59804
0.6566	Remote Similarity	NPC73829
0.6526	Remote Similarity	NPC127056
0.6452	Remote Similarity	NPC127853
0.6346	Remote Similarity	NPC280941
0.6346	Remote Similarity	NPC235772
0.6296	Remote Similarity	NPC120840
0.6296	Remote Similarity	NPC298554
0.6277	Remote Similarity	NPC270667
0.6129	Remote Similarity	NPC473538
0.6125	Remote Similarity	NPC480946
0.6125	Remote Similarity	NPC130577
0.6125	Remote Similarity	NPC142415
0.6125	Remote Similarity	NPC102683
0.6122	Remote Similarity	NPC488516
0.6111	Remote Similarity	NPC323341
0.6105	Remote Similarity	NPC164194
0.6055	Remote Similarity	NPC166422
0.604	Remote Similarity	NPC180550
0.604	Remote Similarity	NPC35405
0.602	Remote Similarity	NPC114441
0.6	Remote Similarity	NPC488209
0.5979	Remote Similarity	NPC12288
0.5962	Remote Similarity	NPC276093
0.596	Remote Similarity	NPC472949
0.5918	Remote Similarity	NPC25605
0.5905	Remote Similarity	NPC324875
0.5905	Remote Similarity	NPC292677
0.59	Remote Similarity	NPC22956
0.5865	Remote Similarity	NPC488515
0.5865	Remote Similarity	NPC119794
0.5859	Remote Similarity	NPC109079
0.5854	Remote Similarity	NPC270768
0.5854	Remote Similarity	NPC59263
0.5854	Remote Similarity	NPC210106
0.5833	Remote Similarity	NPC475611
0.5825	Remote Similarity	NPC139044
0.5825	Remote Similarity	NPC471383
0.5814	Remote Similarity	NPC96580
0.5783	Remote Similarity	NPC158141
0.5769	Remote Similarity	NPC257468
0.5714	Remote Similarity	NPC200752
0.569	Remote Similarity	NPC471385
0.567	Remote Similarity	NPC475472
0.5663	Remote Similarity	NPC275809
0.5638	Remote Similarity	NPC31839
0.5631	Remote Similarity	NPC114304
0.5625	Remote Similarity	NPC219180
0.5596	Remote Similarity	NPC62725
0.5568	Remote Similarity	NPC474727
0.5567	Remote Similarity	NPC191410
0.5556	Remote Similarity	NPC488564
0.5545	Remote Similarity	NPC480424
0.5536	Remote Similarity	NPC133818
0.5517	Remote Similarity	NPC296164
0.551	Remote Similarity	NPC480938
0.5487	Remote Similarity	NPC251263
0.5476	Remote Similarity	NPC282616
0.5476	Remote Similarity	NPC84319
0.5476	Remote Similarity	NPC52021
0.5476	Remote Similarity	NPC599947
0.5463	Remote Similarity	NPC75318
0.5455	Remote Similarity	NPC477195
0.5437	Remote Similarity	NPC80843
0.5432	Remote Similarity	NPC604575
0.5426	Remote Similarity	NPC57362
0.5412	Remote Similarity	NPC231063
0.5412	Remote Similarity	NPC282395
0.5412	Remote Similarity	NPC481360
0.5412	Remote Similarity	NPC110308
0.5405	Remote Similarity	NPC288205
0.5405	Remote Similarity	NPC51465
0.53	Remote Similarity	NPC22676
0.5294	Remote Similarity	NPC182797
0.5294	Remote Similarity	NPC161717
0.5294	Remote Similarity	NPC156981
0.5294	Remote Similarity	NPC52169
0.5294	Remote Similarity	NPC488562
0.5275	Remote Similarity	NPC188833
0.5238	Remote Similarity	NPC242840
0.5233	Remote Similarity	NPC106112
0.5233	Remote Similarity	NPC261935
0.5176	Remote Similarity	NPC198664
0.514	Remote Similarity	NPC473383
0.5138	Remote Similarity	NPC484832
0.5133	Remote Similarity	NPC476992
0.513	Remote Similarity	NPC284449
0.5128	Remote Similarity	NPC54636
0.5116	Remote Similarity	NPC121798
0.5116	Remote Similarity	NPC37038
0.5116	Remote Similarity	NPC234346
0.5114	Remote Similarity	NPC474963
0.5098	Remote Similarity	NPC198621
0.5098	Remote Similarity	NPC216940
0.5091	Remote Similarity	NPC37134
0.5056	Remote Similarity	NPC608622
0.5051	Remote Similarity	NPC256798
0.505	Remote Similarity	NPC90856
0.505	Remote Similarity	NPC171007
0.505	Remote Similarity	NPC190849
0.5048	Remote Similarity	NPC295371

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC100383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5646
0.1-0.2	3427
0.2-0.3	67
0.3-0.4	8
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