NPASS Compound

Natural Product: NPC470058

Natural Product ID	NPC470058
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Chisopanin F
IUPAC Name	[(3R,5R,7R,8R,9R,10S,13S,17R)-7-hydroxy-17-[(2S,3S,5R)-5-[(1S)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms	Chisopanin F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1668611
PubChem CID	53326604
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 97101 0 0 0 0 0 0 0 0999 V2000 -5.0601 1.9938 -3.2855 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6085 0.8683 -2.6053 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4279 1.0248 -1.2868 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4271 0.2732 -0.6139 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0910 0.6095 0.6773 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6484 0.1602 0.7092 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1393 0.7113 -0.6468 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3025 -0.3392 -1.2410 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9062 -0.2368 -2.6509 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7552 0.6652 -2.6591 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1608 0.5415 -1.4848 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9163 -0.4662 -0.6420 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4722 -1.8713 -0.9492 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7605 -0.1415 0.7801 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6954 -0.3380 1.1661 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5987 0.1228 0.0964 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0502 1.1568 -0.8389 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6668 2.4604 -0.2720 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0276 1.3806 -1.9688 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0048 0.3459 -2.9024 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4325 1.6319 -1.5057 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8533 0.4336 -0.6774 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0203 0.4290 0.5677 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1390 1.6227 1.4217 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4833 -0.7808 1.3751 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9047 -0.6832 1.7944 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8344 -0.0054 0.8358 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3036 0.2578 -0.5181 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8347 -0.8552 -1.4439 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9981 1.5223 -1.0547 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9903 -0.8418 0.7420 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2534 -0.4759 1.1130 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4496 0.6569 1.5689 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3783 -1.4262 0.9712 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9617 0.1384 1.7588 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2948 -1.3017 1.8406 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8245 -1.8571 0.6811 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0183 -1.2894 0.3132 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3848 -1.4155 2.9426 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1243 -2.0738 2.3955 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4392 0.5737 2.9773 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1721 1.7472 -4.3612 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9410 2.4610 -2.8469 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2359 2.7551 -3.2326 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7004 2.0936 -1.0249 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0346 1.7365 0.7741 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6043 -0.9404 0.6717 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2016 0.6421 1.5679 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5566 1.6369 -0.5181 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8280 -1.3288 -1.0953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4817 -1.2545 -2.9311 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6595 -0.0605 -3.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4113 1.3394 -3.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0392 -2.3857 -0.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3468 -2.5511 -1.1855 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1398 -1.9280 -1.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3366 -0.8452 1.4062 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9545 0.9208 1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8762 -1.4007 1.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8407 0.1910 2.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7682 -0.7864 -0.5699 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3906 2.7458 -0.5578 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7248 2.6023 0.8005 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2755 3.3033 -0.7190 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6871 2.3070 -2.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2815 0.7496 -3.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0702 1.6040 -2.4340 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6056 2.5923 -1.0392 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4757 -0.4410 -1.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3389 1.5569 2.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0763 1.5772 2.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1156 2.5948 0.9364 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8478 -0.7765 2.3024 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2548 -1.6757 0.7838 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9826 -0.1289 2.7764 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2382 -1.7291 2.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2557 0.9528 1.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2907 -1.7801 -1.0958 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5533 -0.6887 -2.4827 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8947 -1.0454 -1.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0571 1.4408 -0.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5930 2.4335 -0.6200 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0830 1.4964 -2.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2861 -0.8524 0.6714 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5767 -1.8693 1.9894 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1569 -2.2511 0.2700 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9327 0.7197 1.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3629 -1.7924 -0.6311 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9910 -0.2125 0.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8390 -1.5443 1.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7793 -2.4384 2.9792 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1424 -0.6296 2.8158 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8629 -1.2218 3.9033 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3503 -1.4194 2.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6957 -2.7909 1.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4309 -2.7531 3.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3383 1.5388 2.9988 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 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 1 0 10 11 2 0 11 12 1 0 12 13 1 1 12 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 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 27 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 5 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 36 40 1 0 35 41 1 0 7 3 1 0 12 8 1 0 23 16 1 0 17 11 1 0 28 22 1 0 1 42 1 0 1 43 1 0 1 44 1 0 3 45 1 6 5 46 1 6 6 47 1 0 6 48 1 0 7 49 1 1 8 50 1 6 9 51 1 0 9 52 1 0 10 53 1 0 13 54 1 0 13 55 1 0 13 56 1 0 14 57 1 0 14 58 1 0 15 59 1 0 15 60 1 0 16 61 1 6 18 62 1 0 18 63 1 0 18 64 1 0 19 65 1 6 20 66 1 0 21 67 1 0 21 68 1 0 22 69 1 6 24 70 1 0 24 71 1 0 24 72 1 0 25 73 1 0 25 74 1 0 26 75 1 0 26 76 1 0 27 77 1 1 29 78 1 0 29 79 1 0 29 80 1 0 30 81 1 0 30 82 1 0 30 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 35 87 1 6 38 88 1 0 38 89 1 0 38 90 1 0 39 91 1 0 39 92 1 0 39 93 1 0 40 94 1 0 40 95 1 0 40 96 1 0 41 97 1 0 M END

Standard InCHIKey	SABPQJQTNUXWFJ-LFUNMFHISA-N
Standard InCHI	InChI=1S/C34H56O7/c1-19(35)40-27-14-16-33(7)24-13-15-32(6)21(20-17-22(41-29(20)38-9)28(37)31(4,5)39-10)11-12-23(32)34(24,8)26(36)18-25(33)30(27,2)3/h12,20-22,24-29,36-37H,11,13-18H2,1-10H3/t20-,21+,22+,24+,25-,26+,27+,28-,29-,32-,33+,34-/m0/s1
SMILES	CO[C@H]1O[C@H](C[C@H]1[C@H]1CC=C2[C@@]1(C)CC[C@H]1[C@@]2(C)[C@H](O)C[C@@H]2[C@]1(C)CC[C@H](C2(C)C)OC(=O)C)[C@@H](C(OC)(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.4	Volume:	610.096 ? Van der Waals volume.
Dense:	0.945	LogP:	3.737 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.764 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.997 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	26.0
TPSA:	94.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.311	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.479	Fsp³:	0.912
MCE-18:	105.969 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.84	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.244	Promiscuous compounds:	0.366

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.132	MDCK Permeability:	-4.896
Pgp-inhibitor:	0.995	Pgp-substrate:	0.861
PAMPA:	0.481 ? 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%):	0.849	30% Bioavailability (F30%):	0.731
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.839
Plasma Protein Binding (PPB):	77.528%	Volume Distribution (VD):	-0.158
Fu:	16.259% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.119
BSEP inhibitor:	0.955

ADMET: Metabolism

CYP1A2-inhibitor:	0.015	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.428	CYP2C19-substrate:	0.009
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.982	CYP3A4-substrate:	0.158
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.935
HLM stability:	0.993 ? 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):

11.191

Half-life (T1/2):

0.782

ADMET: Toxicity

hERG Blockers:	0.081	hERG Blockers (10um):	0.423
Human Hepatotoxicity (H-HT):	0.527	Drug-induced Liver Injury (DILI):	0.642
AMES Toxicity:	0.702	Rat Oral Acute Toxicity:	0.699
Maximum Recommended Daily Dose:	0.645	Skin Sensitization:	0.991
Carcinogencity:	0.666	Eye Corrosion:	0.009
Eye Irritation:	0.428	Respiratory Toxicity:	0.619
Drug-induced Neurotoxicity:	0.232	Ototoxicity:	0.678
Hematotoxicity:	0.47	Drug-induced Nephrotoxicity:	0.804
Genotoxicity:	0.737	RPMI-8226 Immunitoxicity:	0.142
A549 Cytotoxicity:	0.795	Hek293 Cytotoxicity:	0.56
BCF:	1.592 ? 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:	4.021 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.733 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.007 ? 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
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943621]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Yunnan, China	2007-May	PMID[21288727]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32208696]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19151	Chisocheton paniculatus	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
IC50	2

Activity Type	# Activity
Cell line	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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	6900.0	nM	PMID[19926364]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[19943621]

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 NPC470058 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	18350
0.1-0.2	25111
0.2-0.3	6142
0.3-0.4	219
0.4-0.5	17
0.5-0.6	6
0.6-0.7	3
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470057
0.9028	High Similarity	NPC470062
0.9028	High Similarity	NPC470061
0.8472	Intermediate Similarity	NPC470055
0.8472	Intermediate Similarity	NPC470064
0.8472	Intermediate Similarity	NPC470043
0.7632	Intermediate Similarity	NPC470060
0.7632	Intermediate Similarity	NPC470059
0.7632	Intermediate Similarity	NPC470056
0.6375	Remote Similarity	NPC470065
0.6049	Remote Similarity	NPC470067
0.6	Remote Similarity	NPC470068
0.5854	Remote Similarity	NPC470054
0.5488	Remote Similarity	NPC470063
0.5432	Remote Similarity	NPC484782
0.5294	Remote Similarity	NPC302471
0.5053	Remote Similarity	NPC478549
0.5053	Remote Similarity	NPC478550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6974
0.1-0.2	2079
0.2-0.3	97
0.3-0.4	0
0.4-0.5	0
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