NPASS Compound

Natural Product: NPC73038

Natural Product ID	NPC73038
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lamesticumin B
IUPAC Name	methyl 3-[(1R,2S,6R)-2-[2-[(1S,4aR,6S,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-6-(2-hydroxypropan-2-yl)-1,3-dimethylcyclohex-3-en-1-yl]propanoate
Synonyms	Lamesticumin B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1782130
PubChem CID	53262847
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

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 87 89 0 0 0 0 0 0 0 0999 V2000 5.8717 4.5813 -0.4916 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2679 3.6411 -1.3173 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2080 2.7894 -0.8394 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9380 3.0075 0.3355 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6400 1.8419 -1.7751 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5768 0.9340 -1.5896 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3973 -0.1841 -0.6411 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0814 -0.9233 -1.0405 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9990 0.2647 0.7728 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0370 1.3502 0.9248 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3173 1.4977 0.4735 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4545 0.6938 0.8909 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8290 0.7748 2.3497 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4638 1.7040 3.1791 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7310 -0.3097 2.8254 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9837 -0.3829 1.9586 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5857 -0.3121 0.5249 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7575 0.9118 0.1590 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3840 2.1901 0.6751 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7194 0.9796 -1.3117 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7644 -0.4182 -1.9434 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2090 -0.8833 -1.7937 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7213 -0.6172 -0.4089 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2518 -1.9829 0.0924 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8838 0.2990 -0.3137 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9430 -0.2380 -2.7926 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9266 -0.8606 1.7251 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0164 -1.6567 1.7715 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1232 -1.2834 0.8577 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5455 -1.1044 -0.5626 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5673 -2.4277 -1.1940 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8778 -2.9225 -0.8540 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6714 -3.4994 -0.6694 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5482 -2.4932 -2.6815 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8137 -1.2021 2.6473 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9758 4.5759 -0.7260 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6632 4.4681 0.5763 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5300 5.5998 -0.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3363 2.5462 -2.6662 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5790 1.4177 -2.2916 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2845 0.4959 -2.6198 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6520 1.6097 -1.4470 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3507 -0.2489 -1.5006 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6393 -1.4625 -0.2209 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3076 -1.6552 -1.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9981 0.7561 1.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5730 2.3640 0.8253 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9382 1.3802 2.0917 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6320 2.5811 0.8602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4674 1.7044 -0.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2193 -0.3848 0.6655 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8431 2.5713 2.9933 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8089 1.6438 4.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2267 -1.2852 2.8296 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0874 -0.1302 3.8604 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3809 -1.4241 2.1196 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7703 0.2958 2.2744 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8699 -1.1827 0.3728 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1783 2.0408 1.4066 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7950 2.8116 -0.1510 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6246 2.8537 1.1745 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0051 1.6255 -1.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7118 1.4457 -1.6254 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0492 -1.1041 -1.4936 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.3059 -3.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2004 -1.9560 -2.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0055 -1.8436 0.8717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3966 -2.6203 0.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7270 -2.5059 -0.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7013 1.3636 -0.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6230 -0.0193 -1.0903 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4057 0.0673 0.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3321 0.6110 -2.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0452 -2.4995 2.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6553 -0.3801 1.2160 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8993 -2.0751 0.8453 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4036 -0.4985 -1.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9818 -3.7996 -1.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0736 -3.2949 0.2048 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9478 -3.8960 -1.4500 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2143 -4.4640 -0.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7270 -3.0900 -3.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4666 -1.4922 -3.1833 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4756 -2.9258 -3.1279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5559 -0.3560 3.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0131 -1.7108 2.1639 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1975 -1.9773 3.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 7 6 1 6 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 22 26 1 0 9 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 31 34 1 0 27 35 1 0 30 7 1 0 18 12 1 0 23 17 1 0 1 36 1 0 1 37 1 0 1 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 1 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 1 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 1 19 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 22 66 1 6 24 67 1 0 24 68 1 0 24 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 30 77 1 6 32 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 35 85 1 0 35 86 1 0 35 87 1 0 M END

Standard InCHIKey	KYHATJJXUGJUJJ-LUFVGXTESA-N
Standard InCHI	InChI=1S/C31H52O4/c1-20-10-14-24-28(3,4)26(32)16-18-30(24,7)22(20)12-13-23-21(2)11-15-25(29(5,6)34)31(23,8)19-17-27(33)35-9/h11,22-26,32,34H,1,10,12-19H2,2-9H3/t22-,23-,24-,25-,26-,30+,31+/m0/s1
SMILES	COC(=O)CC[C@]1(C)[C@@H](CC[C@H]2C(=C)CC[C@@H]3[C@]2(C)CC[C@@H](C3(C)C)O)C(=CC[C@H]1C(O)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.39	Volume:	546.314 ? Van der Waals volume.
Dense:	0.894	LogP:	5.076 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.128 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.992 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	19.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.304	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.939	Fsp³:	0.839
MCE-18:	71.228 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.743	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.649	Promiscuous compounds:	0.358

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.778	MDCK Permeability:	-4.762
Pgp-inhibitor:	0.886	Pgp-substrate:	0.001
PAMPA:	0.026 ? 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%):	0.007	30% Bioavailability (F30%):	0.016
50% Bioavailability (F50%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.221	MRP1:	0.68
Plasma Protein Binding (PPB):	83.296%	Volume Distribution (VD):	-0.37
Fu:	14.236% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.993
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.249
CYP2C19-inhibitor:	0.907	CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.942	CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.995 ? 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):

11.319

Half-life (T1/2):

0.882

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.138
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.057
AMES Toxicity:	0.164	Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.594	Skin Sensitization:	0.79
Carcinogencity:	0.825	Eye Corrosion:	0.023
Eye Irritation:	0.606	Respiratory Toxicity:	0.474
Drug-induced Neurotoxicity:	0.05	Ototoxicity:	0.634
Hematotoxicity:	0.276	Drug-induced Nephrotoxicity:	0.87
Genotoxicity:	0.03	RPMI-8226 Immunitoxicity:	0.079
A549 Cytotoxicity:	0.005	Hek293 Cytotoxicity:	0.187
BCF:	1.962 ? 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:	4.86 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.298 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.724 ? 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
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	exocarp	n.a.	DOI[10.1021/jo00172a004]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444710]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[19299148]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Mengla County, Yunnan Province, China	2005-AUG	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[30335380]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20633	Lansium domesticum	Species	Meliaceae	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
MIC	11

Activity Type	# Activity
Organism	11

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
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	3.12	ug.mL-1	PMID[21401117]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[21401117]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.12	ug.mL-1	PMID[21401117]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[21401117]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.12	ug.mL-1	PMID[21401117]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[21401117]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[21401117]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	=	12.5	ug.mL-1	PMID[21401117]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3.12	ug.mL-1	PMID[21401117]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	50.0	ug.mL-1	PMID[21401117]
NPT2227	Organism	Alcaligenes faecalis	Alcaligenes faecalis	MIC	>	50.0	ug.mL-1	PMID[21401117]

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 NPC73038 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	14842
0.1-0.2	26459
0.2-0.3	7897
0.3-0.4	607
0.4-0.5	41
0.5-0.6	7
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8246	Intermediate Similarity	NPC234974
0.7097	Intermediate Similarity	NPC325594
0.5821	Remote Similarity	NPC10349
0.5797	Remote Similarity	NPC321514
0.5763	Remote Similarity	NPC470428
0.5625	Remote Similarity	NPC478375
0.5397	Remote Similarity	NPC482141
0.5397	Remote Similarity	NPC482142
0.5397	Remote Similarity	NPC608380

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC73038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6358
0.1-0.2	2662
0.2-0.3	126
0.3-0.4	3
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