NPASS Compound

Natural Product: NPC43353

Natural Product ID	NPC43353
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Beta-Caffeoyl-12-Oleanen-28-Oic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aS,10S,12aS,14bS)-10-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,2,6a,6b,9,9,12a-heptamethyl-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	CHEMBL449798
PubChem CID	44566355
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 98103 0 0 0 0 0 0 0 0999 V2000 4.9497 -2.3324 1.5911 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7838 -1.7327 0.4757 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4789 -1.7664 -0.2229 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5513 -2.6186 0.5787 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1030 -2.3670 0.3444 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7560 -0.8775 0.5642 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5389 -0.1826 -0.4920 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0172 -0.3687 -0.4695 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7220 0.6392 0.4183 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4747 -0.0353 -1.9052 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1468 1.2607 -0.6809 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2694 1.2179 -1.2172 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1831 0.5871 -0.2181 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7164 -0.7094 0.3620 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5382 -1.0408 1.5799 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9132 -0.5697 1.4036 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4361 0.0478 0.3258 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5517 0.2958 -0.8316 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3886 -0.8942 -1.7588 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1005 1.4166 -1.6227 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5066 1.1024 -2.0367 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4565 0.7687 -0.9442 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8491 0.4487 0.3746 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6822 -0.3784 1.2988 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1460 -0.4504 1.0581 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9140 0.4707 1.9875 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6623 -1.8616 1.4320 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5449 -0.2993 -0.3863 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3583 -0.4076 -1.3152 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3478 1.9931 -0.8476 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3529 2.6366 0.2138 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1062 2.3473 -1.9129 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3871 1.6360 0.8649 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1481 -0.6283 1.9734 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9593 -1.0188 -0.0595 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1105 -1.0077 0.5849 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3089 -0.3309 0.1262 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3839 0.3823 -1.0376 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5858 0.9836 -1.3680 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7055 0.8895 -0.5686 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6412 0.1715 0.6097 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4462 -0.4253 0.9362 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7644 0.0599 1.4412 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8952 1.5176 -0.9513 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6735 -2.3287 -1.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7849 -2.5581 1.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7242 -3.7048 0.3215 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5331 -2.9160 1.1313 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7511 -2.6589 -0.6432 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2002 -0.6808 -1.4599 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2904 0.1544 1.2564 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4914 1.2406 -0.1275 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0539 1.3733 0.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1445 0.8338 -1.9171 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0301 -0.8906 -2.3557 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6156 0.2082 -2.5638 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2453 1.8949 0.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7857 1.6819 -1.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2540 0.7855 -2.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5861 2.2907 -1.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0040 -1.5345 -0.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0678 -0.6824 2.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5747 -2.1622 1.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6753 -0.6902 2.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3455 -0.9311 -2.2033 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9865 -0.7795 -2.7142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7257 -1.8431 -1.3432 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5075 1.4972 -2.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1145 2.4074 -1.1614 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6140 0.3036 -2.7982 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8295 2.0297 -2.6288 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8099 1.4782 0.8838 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5636 -0.0244 2.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3187 -1.4495 1.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7852 0.9402 1.4709 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2357 1.2613 2.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3372 -0.0483 2.8716 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7410 -1.9438 1.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4802 -1.9341 2.5269 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0589 -2.6320 0.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9737 0.7143 -0.5048 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3042 -1.0152 -0.7331 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7762 -1.3284 -1.1624 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7366 -0.3299 -2.3495 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6632 3.2143 -1.9654 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6146 2.4472 0.8230 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3495 2.1676 0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3204 1.2333 1.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7772 -1.5110 2.5807 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2427 -0.6587 2.1517 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7758 0.2632 2.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9136 -0.4845 -0.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1361 -1.5474 1.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5150 0.4614 -1.6682 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6270 1.5417 -2.2894 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3866 -1.0005 1.8750 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8426 -0.8407 1.9211 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7529 1.0243 -0.8770 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 7 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 6 18 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 25 27 1 0 25 28 1 0 28 29 1 0 22 30 1 1 30 31 2 0 30 32 1 0 13 33 1 1 6 34 1 1 2 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 41 43 1 0 40 44 1 0 8 3 1 0 18 13 1 0 29 22 1 0 42 37 1 0 14 6 1 0 23 17 1 0 3 45 1 6 4 46 1 0 4 47 1 0 5 48 1 0 5 49 1 0 7 50 1 6 9 51 1 0 9 52 1 0 9 53 1 0 10 54 1 0 10 55 1 0 10 56 1 0 11 57 1 0 11 58 1 0 12 59 1 0 12 60 1 0 14 61 1 6 15 62 1 0 15 63 1 0 16 64 1 0 19 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 20 69 1 0 21 70 1 0 21 71 1 0 23 72 1 1 24 73 1 0 24 74 1 0 26 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 29 83 1 0 29 84 1 0 32 85 1 0 33 86 1 0 33 87 1 0 33 88 1 0 34 89 1 0 34 90 1 0 34 91 1 0 35 92 1 0 36 93 1 0 38 94 1 0 39 95 1 0 42 96 1 0 43 97 1 0 44 98 1 0 M END

Standard InCHIKey	KFFZENNMYQOFQK-SXXKULMJSA-N
Standard InCHI	InChI=1S/C39H54O5/c1-34(2)18-20-39(33(43)44)21-19-37(6)25(27(39)23-34)10-13-32-36(5)16-14-26(35(3,4)31(36)15-17-38(32,37)7)28(40)11-8-24-9-12-29(41)30(42)22-24/h8-12,22,26-27,31-32,41-42H,13-21,23H2,1-7H3,(H,43,44)/b11-8+/t26-,27+,31+,32-,36+,37-,38-,39+/m1/s1
SMILES	O=C([C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C)/C=C/c1ccc(c(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.4	Volume:	657.257 ? Van der Waals volume.
Dense:	0.917	LogP:	4.646 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.88 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.39 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	35.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.181	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.913	Fsp³:	0.692
MCE-18:	165.879 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.984	Fluc inhibitor:	0.773 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.035 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.058 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.301	Promiscuous compounds:	0.093

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.485	MDCK Permeability:	-5.014
Pgp-inhibitor:	0.022	Pgp-substrate:	0.0
PAMPA:	0.996 ? 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%):	0.787	30% Bioavailability (F30%):	0.323
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.48
Plasma Protein Binding (PPB):	98.16%	Volume Distribution (VD):	-0.265
Fu:	1.461% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.007
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.181	CYP2C19-substrate:	0.259
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.272	CYP3A4-substrate:	0.665
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.901
HLM stability:	0.237 ? 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):

4.384

Half-life (T1/2):

1.124

ADMET: Toxicity

hERG Blockers:	0.105	hERG Blockers (10um):	0.176
Human Hepatotoxicity (H-HT):	0.775	Drug-induced Liver Injury (DILI):	0.879
AMES Toxicity:	0.254	Rat Oral Acute Toxicity:	0.361
Maximum Recommended Daily Dose:	0.786	Skin Sensitization:	0.996
Carcinogencity:	0.791	Eye Corrosion:	0.009
Eye Irritation:	0.571	Respiratory Toxicity:	0.884
Drug-induced Neurotoxicity:	0.031	Ototoxicity:	0.812
Hematotoxicity:	0.191	Drug-induced Nephrotoxicity:	0.751
Genotoxicity:	0.942	RPMI-8226 Immunitoxicity:	0.017
A549 Cytotoxicity:	0.683	Hek293 Cytotoxicity:	0.327
BCF:	1.818 ? 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:	4.802 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.14 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.59 ? 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
NPO6918	Geranium niveum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346950]
NPO6918	Geranium niveum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6918	Geranium niveum	Species	Geraniaceae	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	3

Activity Type	# Activity
Organism	3

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
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	22.6	ug.mL-1	PMID[25237727]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	19.25	ug.mL-1	PMID[18068979]
NPT2645	Organism	Giardia intestinalis	Giardia intestinalis	IC50	=	31.2	ug.mL-1	PMID[25136754]

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 NPC43353 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	11216
0.1-0.2	35706
0.2-0.3	2481
0.3-0.4	282
0.4-0.5	132
0.5-0.6	34
0.6-0.7	3
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	Natural Product ID
0.6526	Remote Similarity	NPC132126
0.6042	Remote Similarity	NPC22676
0.602	Remote Similarity	NPC606782
0.5979	Remote Similarity	NPC198621
0.5979	Remote Similarity	NPC216940
0.59	Remote Similarity	NPC610795
0.5833	Remote Similarity	NPC475627
0.5758	Remote Similarity	NPC605663
0.5647	Remote Similarity	NPC200752
0.5529	Remote Similarity	NPC158141
0.5524	Remote Similarity	NPC601567
0.5524	Remote Similarity	NPC606631
0.5437	Remote Similarity	NPC475311
0.537	Remote Similarity	NPC53520
0.5366	Remote Similarity	NPC604575
0.53	Remote Similarity	NPC171007
0.53	Remote Similarity	NPC190849
0.5294	Remote Similarity	NPC480946
0.5294	Remote Similarity	NPC130577
0.5294	Remote Similarity	NPC142415
0.5294	Remote Similarity	NPC102683
0.5287	Remote Similarity	NPC298554
0.5253	Remote Similarity	NPC18982
0.5233	Remote Similarity	NPC270768
0.5233	Remote Similarity	NPC59263
0.5233	Remote Similarity	NPC210106
0.5196	Remote Similarity	NPC262970
0.5172	Remote Similarity	NPC231063
0.5172	Remote Similarity	NPC282395
0.5143	Remote Similarity	NPC482051
0.5114	Remote Similarity	NPC120840
0.5098	Remote Similarity	NPC477873
0.5094	Remote Similarity	NPC479745
0.5057	Remote Similarity	NPC84319
0.5057	Remote Similarity	NPC156981
0.5057	Remote Similarity	NPC52021
0.5057	Remote Similarity	NPC599947

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC43353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3647
0.1-0.2	5451
0.2-0.3	51
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
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
0.602	Remote Similarity	NPD8166	Discontinued

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