NPASS Compound

Natural Product: NPC477873

Natural Product ID	NPC477873
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S,4aS,6aR,6aS,6bR,8aR,10R,12aR,14bR)-10-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-2,6a,6b,9,9,12a-hexamethyl-3,4,4a,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-2-carboxylic acid
IUPAC Name	(2S,4aS,6aR,6aS,6bR,8aR,10R,12aR,14bR)-10-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-2,6a,6b,9,9,12a-hexamethyl-3,4,4a,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44577082
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 96101 0 0 0 0 0 0 0 0999 V2000 -6.1013 3.7111 0.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3767 2.4045 0.0202 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9903 1.4659 0.9799 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1408 0.1132 0.4182 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1800 -0.3558 -0.6102 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7828 -1.7895 -0.3697 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4889 -2.1143 0.2383 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3850 -1.0643 0.1498 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8223 -0.2507 -1.0042 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0674 -0.2490 -2.0720 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7951 -0.9970 -2.2412 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1426 -0.8611 -0.8862 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9877 -1.6075 0.0762 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2869 -1.4714 1.4406 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1718 -1.8778 1.3886 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8317 -0.8986 0.4763 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3216 -1.1332 -0.9086 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0109 -0.0114 -1.7071 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4890 -0.2623 -1.8034 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1152 -0.9209 -0.6158 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3015 -0.7415 0.6339 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8040 -1.7952 1.6328 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7036 0.5956 1.2287 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3806 -0.3249 -0.4088 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5333 -1.0931 -0.4089 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4154 -2.3539 -0.6012 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8563 -0.5340 -0.2024 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9968 0.7519 -0.0080 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2768 1.4122 0.2079 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4655 0.7497 0.2303 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6719 1.3981 0.4357 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6698 2.7682 0.6259 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4870 3.4653 0.6090 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3068 2.7876 0.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8547 3.4648 0.8361 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8594 0.6921 0.4510 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7446 -2.4013 -1.5524 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0428 -3.0905 -0.1323 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0720 0.5422 -1.0338 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0134 1.8881 -0.3974 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5348 -0.3429 1.4708 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2205 2.7615 -1.1261 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3725 2.3059 -1.3392 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7267 3.6686 -2.0566 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0110 3.9517 1.3820 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2787 3.5358 1.4988 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8301 4.5149 0.0745 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9967 1.8393 1.3130 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3777 1.5011 1.9186 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0751 -0.5938 1.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2334 -0.0192 0.1359 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8647 -0.4630 -1.5319 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6027 -2.1984 0.3084 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9762 -2.4233 -1.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6495 -2.4546 1.3061 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1879 -3.0880 -0.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3521 0.3489 -2.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1960 -0.6530 -3.0836 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9726 -2.0816 -2.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2283 0.2215 -0.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2273 -0.3900 1.6423 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7272 -2.0986 2.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5428 -1.6265 2.4297 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3857 -2.9204 1.2523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3965 0.1114 0.7684 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7929 0.9544 -1.1685 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6453 0.0859 -2.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9420 0.7663 -1.8955 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7920 -0.7513 -2.7727 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2967 -2.0005 -0.7401 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5322 -1.3899 2.6437 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9024 -1.7711 1.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4126 -2.7887 1.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4453 1.1282 0.6015 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 1.2432 1.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1485 0.5060 2.2415 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7060 -1.1774 -0.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0712 1.3484 -0.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5111 -0.3196 0.0882 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5221 4.5336 0.7607 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4034 3.3862 0.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7352 3.0008 0.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9324 -0.2697 0.7786 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1152 -2.8075 -2.1226 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1933 -3.1467 -0.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5191 -2.2784 -2.3704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4368 -3.4741 -1.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0113 -3.5620 -0.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5659 -3.5363 0.7357 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2665 0.8238 -2.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3173 1.9943 0.4531 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6471 2.6990 -1.1062 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5980 -0.0426 1.6588 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3779 -1.1116 2.2499 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9317 0.5117 1.6567 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2987 4.0269 -2.8087 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 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 9 10 2 0 10 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 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 20 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 32 35 1 0 31 36 1 0 17 37 1 6 13 38 1 6 9 39 1 0 39 40 1 0 8 41 1 1 2 42 1 0 42 43 2 0 42 44 1 0 40 2 1 0 39 5 1 0 13 8 1 0 17 12 1 0 21 16 1 0 34 29 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 6 6 53 1 0 6 54 1 0 7 55 1 0 7 56 1 0 10 57 1 0 11 58 1 0 11 59 1 0 12 60 1 1 14 61 1 0 14 62 1 0 15 63 1 0 15 64 1 0 16 65 1 1 18 66 1 0 18 67 1 0 19 68 1 0 19 69 1 0 20 70 1 6 22 71 1 0 22 72 1 0 22 73 1 0 23 74 1 0 23 75 1 0 23 76 1 0 27 77 1 0 28 78 1 0 30 79 1 0 33 80 1 0 34 81 1 0 35 82 1 0 36 83 1 0 37 84 1 0 37 85 1 0 37 86 1 0 38 87 1 0 38 88 1 0 38 89 1 0 39 90 1 6 40 91 1 0 40 92 1 0 41 93 1 0 41 94 1 0 41 95 1 0 44 96 1 0 M END

Standard InCHIKey	YXGXPJKLXCGTGN-FDOQKXFTSA-N
Standard InCHI	InChI=1S/C38H52O6/c1-34(2)29-15-20-38(6)30(11-9-26-25-22-35(3,33(42)43)17-13-24(25)14-19-37(26,38)5)36(29,4)18-16-31(34)44-32(41)12-8-23-7-10-27(39)28(40)21-23/h7-10,12,21,24-25,29-31,39-40H,11,13-20,22H2,1-6H3,(H,42,43)/b12-8+/t24-,25-,29+,30-,31-,35+,36+,37-,38-/m1/s1
SMILES	C[C@@]1(CC[C@@H]2CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@H](C5(C)C)OC(=O)/C=C/C6=CC(=C(C=C6)O)O)C)C)[C@@H]2C1)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	604.38	Volume:	648.751 ? Van der Waals volume.
Dense:	0.932	LogP:	5.134 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.004 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.615 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	35.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.138	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.976	Fsp³:	0.684
MCE-18:	159.5 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.988	Fluc inhibitor:	0.909 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.17 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.008 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.264	Promiscuous compounds:	0.064

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.258	MDCK Permeability:	-4.876
Pgp-inhibitor:	0.518	Pgp-substrate:	0.001
PAMPA:	0.702 ? 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%):	1.0	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.983
Plasma Protein Binding (PPB):	94.371%	Volume Distribution (VD):	-0.14
Fu:	5.166% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.521	BCRP inhibitor:	0.008
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.135 ? 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):

1.971

Half-life (T1/2):

1.593

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.125
Human Hepatotoxicity (H-HT):	0.601	Drug-induced Liver Injury (DILI):	0.646
AMES Toxicity:	0.278	Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.871	Skin Sensitization:	1.0
Carcinogencity:	0.708	Eye Corrosion:	0.018
Eye Irritation:	0.532	Respiratory Toxicity:	0.615
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.63
Hematotoxicity:	0.177	Drug-induced Nephrotoxicity:	0.787
Genotoxicity:	0.824	RPMI-8226 Immunitoxicity:	0.019
A549 Cytotoxicity:	0.652	Hek293 Cytotoxicity:	0.411
BCF:	1.457 ? 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:	4.759 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.247 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.709 ? 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
NPO8737	Saussurea muliensis	Species	Asteraceae	Eukaryota	flowers and roots	Muli Autonomous County of Sichuan, China	2005-AUG	PMID[18419156]
NPO8737	Saussurea muliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8737	Saussurea muliensis	Species	Asteraceae	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	4

Activity Type	# Activity
Organism	4

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
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50	ug/ml	PMID[18419156]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50	ug/ml	PMID[18419156]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50	ug/ml	PMID[18419156]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	50	ug/ml	PMID[18419156]

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 NPC477873 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	9132
0.1-0.2	36215
0.2-0.3	3749
0.3-0.4	631
0.4-0.5	87
0.5-0.6	32
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9024	High Similarity	NPC477874
0.6495	Remote Similarity	NPC172311
0.6383	Remote Similarity	NPC182249
0.6383	Remote Similarity	NPC473591
0.6346	Remote Similarity	NPC53520
0.63	Remote Similarity	NPC610795
0.625	Remote Similarity	NPC8102
0.625	Remote Similarity	NPC66894
0.6211	Remote Similarity	NPC173569
0.6186	Remote Similarity	NPC469447
0.6139	Remote Similarity	NPC482051
0.6105	Remote Similarity	NPC485587
0.596	Remote Similarity	NPC22676
0.5876	Remote Similarity	NPC155192
0.5842	Remote Similarity	NPC482052
0.5784	Remote Similarity	NPC132126
0.5769	Remote Similarity	NPC479745
0.5556	Remote Similarity	NPC248287
0.5556	Remote Similarity	NPC234548
0.5534	Remote Similarity	NPC605663
0.5481	Remote Similarity	NPC304110
0.5481	Remote Similarity	NPC25491
0.5481	Remote Similarity	NPC27518
0.5481	Remote Similarity	NPC611516
0.5474	Remote Similarity	NPC473612
0.5253	Remote Similarity	NPC148404
0.5253	Remote Similarity	NPC35212
0.5192	Remote Similarity	NPC488215
0.5189	Remote Similarity	NPC205392
0.5189	Remote Similarity	NPC105942
0.5182	Remote Similarity	NPC601567
0.5182	Remote Similarity	NPC606631
0.514	Remote Similarity	NPC479739
0.514	Remote Similarity	NPC178093
0.5135	Remote Similarity	NPC481234
0.5135	Remote Similarity	NPC118033
0.5135	Remote Similarity	NPC479431
0.5098	Remote Similarity	NPC43353
0.5096	Remote Similarity	NPC171007
0.5096	Remote Similarity	NPC190849
0.5094	Remote Similarity	NPC479744
0.5093	Remote Similarity	NPC324798
0.5093	Remote Similarity	NPC479742
0.5047	Remote Similarity	NPC606782

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3773
0.1-0.2	5308
0.2-0.3	59
0.3-0.4	8
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
0.5047	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