NPASS Compound

Natural Product: NPC487490

Natural Product ID	NPC487490
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XKJHRTCECPCUQH-ILGBDSNMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	132606913
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 101106 0 0 0 0 0 0 0 0999 V2000 -3.7361 -3.1029 2.8738 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4926 -2.7812 1.8603 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9188 -3.8676 0.9107 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9510 -1.3641 1.5870 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4664 -1.4683 1.4808 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7968 -1.1114 0.0512 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6746 -0.1702 -0.3014 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4111 -0.0492 -1.7565 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1672 0.7752 -1.9397 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9182 0.1386 -1.3242 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6925 -1.1228 -2.0824 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5358 -0.8216 -3.4354 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2988 -0.1112 0.1254 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1141 -0.5280 0.9334 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1804 0.6987 0.9247 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6829 0.7510 -0.5063 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5927 1.5551 -0.6173 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5793 2.8317 0.1577 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7015 0.6958 0.0322 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0705 1.2706 -0.2630 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3943 1.3393 -1.7207 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3108 2.1885 -2.3858 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5137 3.6433 -2.2084 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4941 1.9017 -3.8916 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9651 1.6414 -2.0417 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1049 2.1743 -2.9447 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2144 1.1024 -2.8647 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7759 1.1088 -1.4618 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3370 2.4936 -1.2593 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5749 2.1091 -1.8330 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0386 0.5018 0.4234 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8929 1.0241 1.3718 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7767 2.2519 1.6145 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8956 0.2467 2.0871 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0836 -1.0416 1.8914 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0652 -1.8665 2.5734 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1226 -3.2135 2.2345 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9934 -4.1087 2.7912 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8644 -3.6035 3.7567 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8194 -2.2831 4.0996 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9317 -1.3944 3.5250 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7033 -1.8103 5.0680 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7538 -4.5092 4.3278 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4806 -0.9772 0.2441 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8940 1.0847 0.4063 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2084 2.1082 -0.2513 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7875 1.2754 1.7764 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4279 -4.1220 3.0212 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4415 -2.2906 3.5498 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9454 -3.7758 0.5635 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8565 -4.8654 1.4336 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2513 -3.8954 0.0132 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6239 -0.7361 2.4181 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8588 -2.4598 1.7853 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9147 -0.6878 2.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9304 -1.9489 -0.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7343 -0.4913 0.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2333 0.4668 -2.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3153 -1.0684 -2.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3843 1.7551 -1.4732 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9748 0.9596 -3.0349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7725 -1.6802 -1.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4755 -1.8751 -2.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9239 -1.4967 -4.0344 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6048 0.9037 0.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6381 -1.4120 0.4779 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3910 -0.7737 1.9785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8225 1.5428 1.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3708 0.4623 1.6075 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3882 -0.2944 -0.7459 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4215 2.9164 0.9122 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6569 3.7520 -0.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3085 2.8107 0.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -0.3200 -0.4007 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5989 0.6942 1.1373 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1823 2.3194 0.1296 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5184 0.3643 -2.2153 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9005 3.9517 -1.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3468 3.9430 -2.9158 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6350 4.1821 -2.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5784 1.8012 -4.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0266 0.9335 -4.1640 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1326 2.7552 -4.5019 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0663 0.5468 -2.3635 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2762 2.0857 -3.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4387 3.1781 -2.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9190 1.3622 -3.6495 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6104 0.1641 -3.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8293 2.7719 -2.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9703 2.6046 -0.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5603 3.2795 -1.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3511 1.4821 -1.9656 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5167 0.7429 2.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4400 -1.5007 1.1550 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4444 -3.6241 1.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0195 -5.1574 2.5101 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8927 -0.3546 3.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2627 -1.3777 5.8819 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4896 -4.1831 4.9644 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4934 -1.9022 -0.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3343 2.1025 2.1754 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 0 10 11 1 6 11 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 21 30 1 0 20 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 40 42 1 0 39 43 1 0 13 44 1 0 7 45 1 1 45 46 2 0 45 47 1 0 44 4 1 0 44 7 1 0 28 10 1 0 41 36 1 0 28 16 1 0 25 17 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 3 52 1 0 4 53 1 1 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 11 62 1 0 11 63 1 0 12 64 1 0 13 65 1 1 14 66 1 0 14 67 1 0 15 68 1 0 15 69 1 0 16 70 1 6 18 71 1 0 18 72 1 0 18 73 1 0 19 74 1 0 19 75 1 0 20 76 1 1 21 77 1 6 23 78 1 0 23 79 1 0 23 80 1 0 24 81 1 0 24 82 1 0 24 83 1 0 25 84 1 6 26 85 1 0 26 86 1 0 27 87 1 0 27 88 1 0 29 89 1 0 29 90 1 0 29 91 1 0 30 92 1 0 34 93 1 0 35 94 1 0 37 95 1 0 38 96 1 0 41 97 1 0 42 98 1 0 43 99 1 0 44100 1 6 47101 1 0 M END

Standard InCHIKey	XKJHRTCECPCUQH-ILGBDSNMSA-N
Standard InCHI	InChI=1S/C39H54O8/c1-22(2)24-13-16-38(34(45)46)17-18-39(21-40)25(32(24)38)9-11-30-36(5)20-28(33(44)35(3,4)29(36)14-15-37(30,39)6)47-31(43)12-8-23-7-10-26(41)27(42)19-23/h7-8,10,12,19,24-25,28-30,32-33,40-42,44H,1,9,11,13-18,20-21H2,2-6H3,(H,45,46)/b12-8+/t24-,25+,28+,29-,30+,32+,33-,36-,37+,38-,39-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(CO)[C@H](CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)OC(=O)/C=C/c3ccc(c(c3)O)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.38	Volume:	683.628 ? Van der Waals volume.
Dense:	0.951	LogP:	3.527 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.238 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.991 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	35.0
TPSA:	144.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.099	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.313	Fsp³:	0.692
MCE-18:	167.273 ? 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:	0.9	Fluc inhibitor:	0.765 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.031 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.104	Promiscuous compounds:	0.202

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.52	MDCK Permeability:	-5.045
Pgp-inhibitor:	0.0	Pgp-substrate:	0.008
PAMPA:	0.968 ? 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%):	0.979	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.607	MRP1:	0.962
Plasma Protein Binding (PPB):	84.96%	Volume Distribution (VD):	0.036
Fu:	18.02% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.028
BSEP inhibitor:	0.092

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.069
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.548
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):

5.03

Half-life (T1/2):

1.65

ADMET: Toxicity

hERG Blockers:	0.066	hERG Blockers (10um):	0.156
Human Hepatotoxicity (H-HT):	0.732	Drug-induced Liver Injury (DILI):	0.765
AMES Toxicity:	0.379	Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.7	Skin Sensitization:	1.0
Carcinogencity:	0.797	Eye Corrosion:	0.005
Eye Irritation:	0.555	Respiratory Toxicity:	0.747
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.861
Hematotoxicity:	0.199	Drug-induced Nephrotoxicity:	0.575
Genotoxicity:	0.849	RPMI-8226 Immunitoxicity:	0.008
A549 Cytotoxicity:	0.662	Hek293 Cytotoxicity:	0.26
BCF:	0.607 ? 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:	3.745 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.492 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.811 ? 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
NPO40430	Alnus viridis ssp. viridis	Strain	Betulaceae	Eukaryota	Bark	n.a.	n.a.	PMID[28368586]

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
Ratio IC50	2

Activity Type	# Activity
Cell line	3
Others	2

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
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	18500.0	nM	PMID[28368586]
NPT1083	Cell line	A-375	Homo sapiens	IC50	=	11500.0	nM	PMID[28368586]
NPT81	Cell line	A549	Homo sapiens	IC50	=	15400.0	nM	PMID[28368586]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	1.6	n.a.	PMID[28368586]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	1.2	n.a.	PMID[28368586]

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 NPC487490 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	6921
0.1-0.2	37728
0.2-0.3	4789
0.3-0.4	294
0.4-0.5	97
0.5-0.6	15
0.6-0.7	9
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8953	High Similarity	NPC487491
0.809	Intermediate Similarity	NPC486700
0.809	Intermediate Similarity	NPC275312
0.7708	Intermediate Similarity	NPC487488
0.7708	Intermediate Similarity	NPC487489
0.6957	Remote Similarity	NPC290349
0.6842	Remote Similarity	NPC8102
0.6842	Remote Similarity	NPC66894
0.6337	Remote Similarity	NPC132126
0.6211	Remote Similarity	NPC486699
0.62	Remote Similarity	NPC101863
0.6176	Remote Similarity	NPC487492
0.6122	Remote Similarity	NPC248287
0.6122	Remote Similarity	NPC234548
0.5743	Remote Similarity	NPC475138
0.5729	Remote Similarity	NPC486709
0.5714	Remote Similarity	NPC205392
0.5714	Remote Similarity	NPC105942
0.5506	Remote Similarity	NPC151191
0.5347	Remote Similarity	NPC486695
0.5327	Remote Similarity	NPC479744
0.5275	Remote Similarity	NPC488213
0.5229	Remote Similarity	NPC479739
0.5196	Remote Similarity	NPC310621
0.5135	Remote Similarity	NPC479745
0.5098	Remote Similarity	NPC486708
0.5049	Remote Similarity	NPC148404
0.5049	Remote Similarity	NPC35212
0.5048	Remote Similarity	NPC252133

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC487490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3051
0.1-0.2	5989
0.2-0.3	105
0.3-0.4	0
0.4-0.5	5
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