NPASS Compound

Natural Product: NPC190849

Natural Product ID	NPC190849
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Cis-P-Coumaroyl Maslinic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(Z)-3-phenylprop-2-enoyl]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	CHEMBL463995
PubChem CID	16664518
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 -7.8126 -0.6229 -1.6178 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2746 -0.6331 -1.6108 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8716 -1.3646 -2.8672 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7525 0.7856 -1.7208 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9847 1.5588 -0.4477 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5298 0.8287 0.7983 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6767 1.6955 1.6626 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3209 1.1807 1.9916 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6371 0.6629 0.8075 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3322 1.8733 -0.0882 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4920 -0.3389 0.1107 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8694 -1.0676 -0.8332 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4387 -0.9489 -1.2147 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6439 -0.2068 -0.1971 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8248 -0.5804 -0.1493 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9622 -2.0470 -0.1307 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4563 -0.1021 -1.4444 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6795 0.6886 -1.3219 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6276 0.3061 -0.2170 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9378 0.0813 1.1058 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4351 -1.1333 1.8259 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2893 1.2612 2.0475 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4715 0.1980 0.9401 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7994 0.0992 2.2888 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5673 0.6740 2.1469 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3362 -0.1003 1.1036 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7091 -1.4077 1.7525 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4649 -0.7728 -0.5810 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8584 -0.6282 -0.7539 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2494 0.5313 -0.5531 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6535 -1.7723 -1.1254 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9468 -1.7265 -1.2378 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8576 -0.6318 -1.0196 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9411 -0.5323 -1.9107 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9601 0.3670 -1.7918 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8874 1.2230 -0.7070 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8498 1.1591 0.1872 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8347 0.2338 0.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4094 2.0648 -1.2564 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8977 -0.4852 0.4991 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7285 -1.3474 -0.4227 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7922 0.5425 1.5831 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0782 -0.5994 1.9696 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6732 1.5772 1.8915 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2190 -0.8409 -2.6100 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1897 0.3824 -1.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1562 -1.4223 -0.9286 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8732 -0.9993 -3.2011 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6396 -1.2688 -3.6713 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8099 -2.4431 -2.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7120 0.7872 -2.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3549 1.2865 -2.5108 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4411 2.5209 -0.5306 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0538 1.8133 -0.3795 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7061 2.7282 1.2345 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1828 1.8550 2.6702 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7312 2.0781 2.3561 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3964 0.5360 2.8724 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4322 2.4170 0.2768 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3431 1.6341 -1.1532 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1390 2.6585 0.0241 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5184 -1.7960 -1.3314 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4478 -0.3444 -2.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0078 -1.9537 -1.4569 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5901 0.8659 -0.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2245 -2.6427 0.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9331 -2.4086 -1.2058 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9566 -2.4209 0.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7033 0.5400 -1.9875 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6052 -0.9529 -2.1743 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2717 0.5678 -2.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2925 1.1902 -0.1137 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6584 -1.7122 2.3631 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0498 -1.8127 1.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1803 -0.8878 2.6440 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4025 0.9371 3.0780 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3064 1.6041 1.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6097 2.1119 1.8790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3023 1.2864 0.6452 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3719 0.8212 2.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8720 -0.8580 2.7831 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4989 1.7439 1.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1035 0.4927 3.1220 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9961 -2.2134 1.0875 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8504 -1.8268 2.3603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4720 -1.2204 2.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1664 -2.7454 -1.3303 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4616 -2.6752 -1.5449 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9924 -1.2152 -2.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7899 0.4292 -2.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6800 1.9505 -0.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7884 1.8345 1.0471 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0653 0.1745 0.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3188 2.4896 -1.1518 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9391 -1.0440 1.4903 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6398 -1.7289 0.1406 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1921 -2.2894 -0.6448 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3440 1.4434 2.6604 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 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 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 19 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 18 39 1 0 11 40 1 0 40 41 1 0 6 42 1 1 42 43 2 0 42 44 1 0 41 2 1 0 40 6 1 0 26 9 1 0 38 33 1 0 26 14 1 0 23 15 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 7 55 1 0 7 56 1 0 8 57 1 0 8 58 1 0 10 59 1 0 10 60 1 0 10 61 1 0 12 62 1 0 13 63 1 0 13 64 1 0 14 65 1 6 16 66 1 0 16 67 1 0 16 68 1 0 17 69 1 0 17 70 1 0 18 71 1 6 19 72 1 1 21 73 1 0 21 74 1 0 21 75 1 0 22 76 1 0 22 77 1 0 22 78 1 0 23 79 1 6 24 80 1 0 24 81 1 0 25 82 1 0 25 83 1 0 27 84 1 0 27 85 1 0 27 86 1 0 31 87 1 0 32 88 1 0 34 89 1 0 35 90 1 0 36 91 1 0 37 92 1 0 38 93 1 0 39 94 1 0 40 95 1 1 41 96 1 0 41 97 1 0 44 98 1 0 M END

Standard InCHIKey	QYNZDAXHBDWWFS-GZOAODGCSA-N
Standard InCHI	InChI=1S/C39H54O5/c1-34(2)19-21-39(33(42)43)22-20-37(6)26(27(39)23-34)14-15-30-36(5)24-28(40)32(35(3,4)29(36)17-18-38(30,37)7)44-31(41)16-13-25-11-9-8-10-12-25/h8-14,16,27-30,32,40H,15,17-24H2,1-7H3,(H,42,43)/b16-13-/t27-,28+,29-,30+,32-,36-,37+,38+,39-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)/C=Cc3ccccc3)O)[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.4	Volume:	657.257 ? Van der Waals volume.
Dense:	0.917	LogP:	5.572 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.213 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.342 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	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:	0.205	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.87	Fsp³:	0.692
MCE-18:	162.273 ? 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:	0.988	Fluc inhibitor:	0.665 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.143 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.048 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.1	Promiscuous compounds:	0.031

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.352	MDCK Permeability:	-4.976
Pgp-inhibitor:	0.715	Pgp-substrate:	0.0
PAMPA:	0.997 ? 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):	0.002
20% Bioavailability (F20%):	0.517	30% Bioavailability (F30%):	0.354
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197	MRP1:	0.842
Plasma Protein Binding (PPB):	97.995%	Volume Distribution (VD):	-0.197
Fu:	1.354% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.0
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.247
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.192
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.012 ? 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):

3.632

Half-life (T1/2):

0.841

ADMET: Toxicity

hERG Blockers:	0.11	hERG Blockers (10um):	0.145
Human Hepatotoxicity (H-HT):	0.723	Drug-induced Liver Injury (DILI):	0.201
AMES Toxicity:	0.091	Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.302	Skin Sensitization:	0.999
Carcinogencity:	0.14	Eye Corrosion:	0.023
Eye Irritation:	0.708	Respiratory Toxicity:	0.777
Drug-induced Neurotoxicity:	0.149	Ototoxicity:	0.57
Hematotoxicity:	0.054	Drug-induced Nephrotoxicity:	0.945
Genotoxicity:	0.042	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.44	Hek293 Cytotoxicity:	0.169
BCF:	1.248 ? 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:	4.365 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.86 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.311 ? 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
NPO24979	Tetracera boiviniana	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654414]
NPO24979	Tetracera boiviniana	Species	Dilleniaceae	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	2
Inhibition	2
Activity	2

Activity Type	# Activity
Individual protein	4
Non-molecular	1
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	IC50	=	15000.0	nM	PubChem BioAssay data set
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	IC50	=	7500.0	nM	PubChem BioAssay data set
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	89.0	%	PMID[15646539]
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	70.0	%	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[10654414]
NPT26575	Cell line	P388D1	Mus musculus	Activity	=	77.0	%	PMID[10654414]

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 NPC190849 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	9327
0.1-0.2	35003
0.2-0.3	4671
0.3-0.4	566
0.4-0.5	200
0.5-0.6	63
0.6-0.7	18
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC171007
0.8706	High Similarity	NPC605663
0.8043	Intermediate Similarity	NPC601567
0.8043	Intermediate Similarity	NPC606631
0.7021	Intermediate Similarity	NPC304110
0.7021	Intermediate Similarity	NPC25491
0.7021	Intermediate Similarity	NPC27518
0.7021	Intermediate Similarity	NPC611516
0.6882	Remote Similarity	NPC22676
0.6875	Remote Similarity	NPC482051
0.6737	Remote Similarity	NPC488214
0.6535	Remote Similarity	NPC481234
0.6535	Remote Similarity	NPC118033
0.6535	Remote Similarity	NPC479431
0.6531	Remote Similarity	NPC610795
0.6526	Remote Similarity	NPC488215
0.6495	Remote Similarity	NPC132126
0.6429	Remote Similarity	NPC178093
0.6383	Remote Similarity	NPC475138
0.6364	Remote Similarity	NPC324798
0.6364	Remote Similarity	NPC479742
0.6344	Remote Similarity	NPC485587
0.63	Remote Similarity	NPC479745
0.6289	Remote Similarity	NPC198621
0.6289	Remote Similarity	NPC216940
0.6	Remote Similarity	NPC120840
0.5955	Remote Similarity	NPC230151
0.5889	Remote Similarity	NPC233012
0.5882	Remote Similarity	NPC110308
0.5772	Remote Similarity	NPC488210
0.569	Remote Similarity	NPC488211
0.5618	Remote Similarity	NPC296164
0.5612	Remote Similarity	NPC173569
0.5588	Remote Similarity	NPC172311
0.5588	Remote Similarity	NPC482052
0.5581	Remote Similarity	NPC84319
0.5581	Remote Similarity	NPC52021
0.5581	Remote Similarity	NPC599947
0.5545	Remote Similarity	NPC101863
0.5517	Remote Similarity	NPC231063
0.5517	Remote Similarity	NPC282395
0.5517	Remote Similarity	NPC481360
0.5505	Remote Similarity	NPC53520
0.549	Remote Similarity	NPC262970
0.5465	Remote Similarity	NPC480946
0.5465	Remote Similarity	NPC130577
0.5465	Remote Similarity	NPC142415
0.5465	Remote Similarity	NPC102683
0.5455	Remote Similarity	NPC200752
0.5455	Remote Similarity	NPC111466
0.5402	Remote Similarity	NPC282616
0.5361	Remote Similarity	NPC283849
0.5341	Remote Similarity	NPC158141
0.5333	Remote Similarity	NPC479739
0.5323	Remote Similarity	NPC488212
0.53	Remote Similarity	NPC43353
0.5288	Remote Similarity	NPC479744
0.5281	Remote Similarity	NPC298554
0.5248	Remote Similarity	NPC284807
0.5227	Remote Similarity	NPC270768
0.5227	Remote Similarity	NPC59263
0.5227	Remote Similarity	NPC210106
0.5227	Remote Similarity	NPC275809
0.5204	Remote Similarity	NPC28198
0.5204	Remote Similarity	NPC476123
0.5204	Remote Similarity	NPC606107
0.5196	Remote Similarity	NPC477874
0.5185	Remote Similarity	NPC479740
0.5185	Remote Similarity	NPC479741
0.5185	Remote Similarity	NPC469945
0.5169	Remote Similarity	NPC106112
0.5169	Remote Similarity	NPC261935
0.5161	Remote Similarity	NPC474727
0.5138	Remote Similarity	NPC206232
0.5138	Remote Similarity	NPC14515
0.5102	Remote Similarity	NPC204407
0.51	Remote Similarity	NPC286347
0.5098	Remote Similarity	NPC473538
0.5096	Remote Similarity	NPC127853
0.5096	Remote Similarity	NPC477873
0.5094	Remote Similarity	NPC606782
0.5089	Remote Similarity	NPC481235
0.5088	Remote Similarity	NPC488209
0.5056	Remote Similarity	NPC156981
0.505	Remote Similarity	NPC100383
0.5047	Remote Similarity	NPC479747
0.5047	Remote Similarity	NPC479746
0.5047	Remote Similarity	NPC482049
0.5047	Remote Similarity	NPC482050

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC190849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2997
0.1-0.2	5993
0.2-0.3	153
0.3-0.4	6
0.4-0.5	0
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
0.5094	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