NPASS Compound

Natural Product: NPC475138

Natural Product ID	NPC475138
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-E-P-Coumaroylalphitolic Acid
IUPAC Name	(1R,3aS,5aR,5bR,7aR,9R,10R,11aR,11bR,13aR,13bR)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-9-[(E)-3-phenylprop-2-enoyl]oxy-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL499191
PubChem CID	44575994
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 -5.5896 1.2956 2.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0918 0.1649 1.9161 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4026 -0.9454 2.5622 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2839 0.2687 0.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9973 -0.9599 -0.1015 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0298 -0.4922 -1.5415 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5404 -0.1234 -1.6991 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0978 0.4881 -0.4040 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7761 0.1151 0.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9887 1.4025 0.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8203 0.9382 1.2529 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8526 0.3835 0.2105 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4618 -0.5091 -0.7844 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9283 -0.8679 -0.6087 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4222 -1.2744 -1.9931 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9095 -1.4324 -2.0383 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0427 -2.2209 0.1324 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7386 -1.8685 -0.8047 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7179 -1.5923 -1.0682 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3495 -0.8733 0.1060 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4209 -0.0430 0.8827 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1510 1.2409 1.2831 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5480 1.0159 1.7460 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4392 0.3567 0.7743 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6354 -0.3061 -0.3573 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4917 -1.5313 -0.7581 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6295 0.5379 -1.5810 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3891 1.1543 0.1359 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7806 0.9796 0.1933 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1041 0.0408 0.8721 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6003 1.8867 -0.5215 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8487 2.0443 -0.7359 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0118 1.3070 -0.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0094 0.0335 0.1119 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1594 -0.6103 0.5970 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3567 0.0558 0.6479 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3579 1.3651 0.2032 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2544 2.0025 -0.2677 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4390 0.2221 2.9117 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1326 -0.7113 2.2398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2148 0.0288 -2.2085 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5064 0.8384 -2.8289 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8533 0.6031 -3.8712 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1942 2.0384 -2.7827 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5215 1.1315 2.9414 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1879 1.4497 3.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6310 2.2272 2.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2984 -1.0368 3.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7850 -1.8493 2.0774 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0624 1.0925 0.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0362 -1.0209 0.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4737 -1.8910 0.0733 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6557 0.4101 -1.5949 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3143 -1.2743 -2.2448 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1008 1.6073 -0.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9472 -0.2786 1.1520 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5359 2.1426 0.9554 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6026 1.8845 -0.5105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3775 1.8498 1.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0952 0.2625 2.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5893 1.3505 -0.3315 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1364 -0.6337 -2.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0192 -2.2967 -2.2672 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1546 -1.6229 -3.1260 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2917 -2.2939 -1.5023 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6428 -3.0453 -0.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6496 -2.2091 1.1323 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1563 -2.3787 0.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0887 -2.4795 -1.6605 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8216 -2.3952 0.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8965 -1.1091 -2.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1769 -2.6258 -1.1977 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6669 -1.7375 0.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5920 1.6537 2.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0117 1.9535 0.4793 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9322 1.9838 2.1457 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0235 -0.4229 1.3099 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0633 -2.0031 -1.6787 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5405 -2.2190 0.0948 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5175 -1.1778 -1.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6665 0.9969 -1.6403 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5265 -0.0391 -2.5369 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9478 1.3728 -1.6256 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0112 2.7391 -1.0795 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1238 2.9460 -1.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1157 -0.5793 0.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0859 -1.6429 0.9316 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2541 -0.4299 1.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3070 1.8932 0.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2565 3.0307 -0.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1031 -0.5127 2.8736 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9364 -1.4844 2.4268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1244 -0.0011 3.0718 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7954 -1.2685 2.2638 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8890 0.8449 -2.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0740 -0.7647 -2.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2109 0.5468 -2.1213 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8198 2.9077 -3.1426 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 1 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 14 17 1 0 13 18 1 0 18 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 25 27 1 0 24 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 3 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 23 39 1 0 21 40 1 0 13 41 1 0 7 42 1 0 42 43 2 0 42 44 1 0 8 4 1 0 16 7 1 0 14 9 1 0 21 12 1 0 25 20 1 0 38 33 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 5 51 1 0 5 52 1 0 6 53 1 0 6 54 1 0 8 55 1 0 9 56 1 0 10 57 1 0 10 58 1 0 11 59 1 0 11 60 1 0 12 61 1 0 15 62 1 0 15 63 1 0 16 64 1 0 16 65 1 0 17 66 1 0 17 67 1 0 17 68 1 0 18 69 1 0 18 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 22 74 1 0 22 75 1 0 23 76 1 0 24 77 1 0 26 78 1 0 26 79 1 0 26 80 1 0 27 81 1 0 27 82 1 0 27 83 1 0 31 84 1 0 32 85 1 0 34 86 1 0 35 87 1 0 36 88 1 0 37 89 1 0 38 90 1 0 39 91 1 0 40 92 1 0 40 93 1 0 40 94 1 0 41 95 1 0 41 96 1 0 41 97 1 0 44 98 1 0 M END

Standard InCHIKey	QWMHJORATREBPC-HJTIQSDFSA-N
Standard InCHI	InChI=1S/C39H54O5/c1-24(2)26-17-20-39(34(42)43)22-21-37(6)27(32(26)39)14-15-30-36(5)23-28(40)33(35(3,4)29(36)18-19-38(30,37)7)44-31(41)16-13-25-11-9-8-10-12-25/h8-13,16,26-30,32-33,40H,1,14-15,17-23H2,2-7H3,(H,42,43)/b16-13+/t26-,27+,28+,29-,30+,32+,33-,36-,37+,38+,39-/m0/s1
SMILES	CC(=C)C1CCC2(C1C3CCC4C(C3(CC2)C)(CCC5C4(CC(C(C5(C)C)OC(=O)C=CC6=CC=CC=C6)O)C)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.4	Volume:	657.257 ? Van der Waals volume.
Dense:	0.917	LogP:	5.954 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.48 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.735 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.201	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.965	Fsp³:	0.692
MCE-18:	160.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.975	Fluc inhibitor:	0.607 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.025 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.565 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.067	Promiscuous compounds:	0.023

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.227	MDCK Permeability:	-4.926
Pgp-inhibitor:	0.009	Pgp-substrate:	0.0
PAMPA:	0.075 ? 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%):	0.0	30% Bioavailability (F30%):	0.017
50% Bioavailability (F50%):	0.789

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985	MRP1:	1.0
Plasma Protein Binding (PPB):	96.245%	Volume Distribution (VD):	0.05
Fu:	3.119% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.007
OATP1B3 inhibitor:	0.959	BCRP inhibitor:	0.0
BSEP inhibitor:	0.981

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.828	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.943
HLM stability:	0.0 ? 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):

1.509

Half-life (T1/2):

1.563

ADMET: Toxicity

hERG Blockers:	0.12	hERG Blockers (10um):	0.511
Human Hepatotoxicity (H-HT):	0.453	Drug-induced Liver Injury (DILI):	0.284
AMES Toxicity:	0.04	Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.899	Skin Sensitization:	0.339
Carcinogencity:	0.079	Eye Corrosion:	0.001
Eye Irritation:	0.159	Respiratory Toxicity:	0.537
Drug-induced Neurotoxicity:	0.534	Ototoxicity:	0.918
Hematotoxicity:	0.032	Drug-induced Nephrotoxicity:	0.416
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.111	Hek293 Cytotoxicity:	0.379
BCF:	1.637 ? 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:	5.28 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.921 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.13 ? 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
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350157]
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553872]
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3165	Cochlospermum tinctorium	Species	Bixaceae	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	2
Non-molecular	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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2300.0	nM	PMID[21334794]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3800.0	nM	PMID[21334794]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	43000.0	nM	PMID[12350157]

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 NPC475138 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	8322
0.1-0.2	34762
0.2-0.3	6235
0.3-0.4	397
0.4-0.5	90
0.5-0.6	36
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8675	High Similarity	NPC101863
0.6966	Remote Similarity	NPC248287
0.6966	Remote Similarity	NPC234548
0.6813	Remote Similarity	NPC8102
0.6813	Remote Similarity	NPC66894
0.6559	Remote Similarity	NPC486700
0.6559	Remote Similarity	NPC275312
0.6458	Remote Similarity	NPC205392
0.6458	Remote Similarity	NPC105942
0.6421	Remote Similarity	NPC487491
0.6383	Remote Similarity	NPC171007
0.6383	Remote Similarity	NPC190849
0.5895	Remote Similarity	NPC252133
0.5824	Remote Similarity	NPC486709
0.5783	Remote Similarity	NPC4309
0.5743	Remote Similarity	NPC487490
0.5673	Remote Similarity	NPC487488
0.5673	Remote Similarity	NPC487489
0.5647	Remote Similarity	NPC160506
0.5644	Remote Similarity	NPC304110
0.5644	Remote Similarity	NPC25491
0.5644	Remote Similarity	NPC27518
0.5644	Remote Similarity	NPC611516
0.5545	Remote Similarity	NPC605663
0.5534	Remote Similarity	NPC482051
0.5521	Remote Similarity	NPC290349
0.5357	Remote Similarity	NPC488506
0.5357	Remote Similarity	NPC220498
0.534	Remote Similarity	NPC488205
0.5312	Remote Similarity	NPC486699
0.5278	Remote Similarity	NPC481234
0.5278	Remote Similarity	NPC118033
0.5278	Remote Similarity	NPC479431
0.5258	Remote Similarity	NPC486695
0.5238	Remote Similarity	NPC264317
0.5238	Remote Similarity	NPC294438
0.5192	Remote Similarity	NPC487492
0.5185	Remote Similarity	NPC601567
0.5185	Remote Similarity	NPC606631
0.5176	Remote Similarity	NPC213832
0.5155	Remote Similarity	NPC486708
0.5143	Remote Similarity	NPC178093
0.5116	Remote Similarity	NPC271974
0.5116	Remote Similarity	NPC247312
0.5116	Remote Similarity	NPC201655
0.5094	Remote Similarity	NPC324798
0.5094	Remote Similarity	NPC479742
0.5047	Remote Similarity	NPC479745

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475138 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2360
0.1-0.2	6512
0.2-0.3	274
0.3-0.4	1
0.4-0.5	0
0.5-0.6	3
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
0.5647	Remote Similarity	NPD8035	Phase 2
0.5238	Remote Similarity	NPD7520	Phase 1
0.505	Remote Similarity	NPD8034	Phase 2

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