NPASS Compound

Natural Product: NPC469856

Natural Product ID	NPC469856
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Garcimultiflorone F
IUPAC Name	n.a.
Synonyms	Garcimultiflorone F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1215430
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

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 98100 0 0 0 0 0 0 0 0999 V2000 -3.4629 1.8266 -5.9266 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4455 0.9323 -5.2566 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7594 1.3576 -4.2340 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7741 0.5967 -3.5205 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8630 0.5058 -2.0129 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7417 1.8910 -1.4394 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1070 2.9389 -2.0061 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1374 2.0606 -0.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7642 1.1632 0.2989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5956 -0.2374 -0.0565 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3064 -0.2752 -1.5437 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9768 -0.9021 -2.3327 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6860 -1.1816 0.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0075 -1.1866 -0.3318 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8688 -2.3040 0.2120 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1187 -3.3038 -0.6093 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4116 -2.3506 1.5588 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8574 0.0401 -0.2711 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1846 -0.1942 -0.9440 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2957 0.0979 -0.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3838 0.6664 1.0495 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6373 -0.1418 -0.9928 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6896 -0.7382 0.5782 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7667 -1.1288 -0.3575 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0801 -0.2050 -1.4892 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1642 0.8153 -1.0812 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7654 -1.0563 -2.5546 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9959 -1.4520 0.4751 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7713 -2.5724 1.4442 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0476 -2.8597 2.2492 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0793 -3.3191 1.4378 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7475 -3.9480 3.2895 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5262 -1.6704 3.0185 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3994 -3.7609 0.8463 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8556 1.6661 1.0365 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6394 3.1171 0.7622 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 3.9842 0.1622 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4232 3.3649 2.1485 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0402 2.4783 3.0855 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2956 2.8477 4.3813 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1017 4.1212 4.8243 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3710 5.0548 3.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6158 4.6692 2.6289 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5710 6.3580 4.3608 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3594 4.4879 6.1291 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2738 -0.4036 -5.8469 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0351 2.3755 -5.1697 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2016 1.2229 -6.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8719 2.4631 -6.6054 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9893 2.3983 -3.9334 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5521 -0.4245 -3.9186 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2286 1.1255 -3.6880 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1938 -2.2099 0.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8184 -1.0593 1.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9855 -1.4126 -1.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7262 -4.1295 -0.2779 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7442 -3.3475 -1.6296 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0618 -3.2821 2.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5192 -2.4493 1.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2193 -1.4637 2.1812 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0693 0.2410 0.7863 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4571 0.9123 -0.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2141 -0.6007 -1.9381 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1432 -0.1158 1.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6194 1.4864 1.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4029 1.0572 1.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5189 -0.7908 -1.8668 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3235 -0.6717 -0.3038 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1072 0.8404 -1.2198 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1075 0.0195 1.2851 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4427 -1.6144 1.2095 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4587 -2.1213 -0.8096 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.3279 -1.1019 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9113 1.2530 -0.1168 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2004 1.5560 -1.9154 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0519 -1.5629 -3.2193 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5673 -0.4898 -3.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3446 -1.8439 -1.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2502 -0.5493 1.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9005 -1.6483 -0.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0161 -2.3233 2.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0921 -4.3190 1.4742 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6430 -4.1178 3.3376 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3008 -4.8878 3.0400 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0723 -3.6647 4.3027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1700 -0.9929 2.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6925 -1.1426 3.5358 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1734 -2.0745 3.8535 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2380 -4.1609 0.4829 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2657 1.2325 1.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1497 1.4189 2.7957 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6612 2.0816 5.0613 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9882 5.4489 1.9477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0481 7.0860 4.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6541 5.4339 6.3441 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2576 -0.8181 -5.7191 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5489 -0.4034 -6.9399 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9868 -1.1384 -5.3820 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 5 4 1 6 5 6 1 0 6 7 2 0 6 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 2 0 10 13 1 6 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 14 18 1 0 18 19 1 0 19 20 2 3 20 21 1 0 20 22 1 0 10 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 1 0 30 31 1 0 30 32 1 0 30 33 1 0 29 34 1 0 9 35 1 0 8 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 42 44 1 0 41 45 1 0 2 46 1 0 11 5 1 0 43 38 1 0 25 5 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 13 53 1 0 13 54 1 0 14 55 1 6 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 21 64 1 0 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 22 69 1 0 23 70 1 0 23 71 1 0 24 72 1 6 26 73 1 0 26 74 1 0 26 75 1 0 27 76 1 0 27 77 1 0 27 78 1 0 28 79 1 0 28 80 1 0 29 81 1 0 31 82 1 0 32 83 1 0 32 84 1 0 32 85 1 0 33 86 1 0 33 87 1 0 33 88 1 0 34 89 1 0 35 90 1 0 39 91 1 0 40 92 1 0 43 93 1 0 44 94 1 0 45 95 1 0 46 96 1 0 46 97 1 0 46 98 1 0 M END

Standard InCHIKey	YLWXNRUZQJAHRN-CGJQWDJPSA-N
Standard InCHI	InChI=1S/C38H52O8/c1-21(2)11-12-25(23(5)6)19-37-20-26(18-29(41)36(9,10)46)35(7,8)38(34(37)45,16-15-22(3)4)33(44)30(32(37)43)31(42)24-13-14-27(39)28(40)17-24/h11,13-15,17,25-26,29,39-41,43,46H,5,12,16,18-20H2,1-4,6-10H3/t25-,26-,29?,37-,38+/m1/s1
SMILES	CC(=CC[C@]12C(=O)C(=C([C@@](C1=O)(C[C@H](C(=C)C)CC=C(C)C)C[C@H](C2(C)C)CC(C(O)(C)C)O)O)C(=O)c1ccc(c(c1)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.37	Volume:	684.092 ? Van der Waals volume.
Dense:	0.93	LogP:	4.97 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.296 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.036 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	22.0
TPSA:	152.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.054	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.856	Fsp³:	0.553
MCE-18:	110.932 ? 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:	0.841	Fluc inhibitor:	0.071 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.059 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.376 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.445	Promiscuous compounds:	0.147

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.903	MDCK Permeability:	-4.706
Pgp-inhibitor:	0.0	Pgp-substrate:	0.56
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):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.758

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1	MRP1:	0.927
Plasma Protein Binding (PPB):	82.896%	Volume Distribution (VD):	0.122
Fu:	20.246% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.845
OATP1B3 inhibitor:	0.052	BCRP inhibitor:	0.008
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.844	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.987
CYP3A4-inhibitor:	0.102	CYP3A4-substrate:	0.979
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.999 ? 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):

3.663

Half-life (T1/2):

1.93

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.187
Human Hepatotoxicity (H-HT):	0.705	Drug-induced Liver Injury (DILI):	0.387
AMES Toxicity:	0.37	Rat Oral Acute Toxicity:	0.601
Maximum Recommended Daily Dose:	0.603	Skin Sensitization:	0.997
Carcinogencity:	0.655	Eye Corrosion:	0.0
Eye Irritation:	0.027	Respiratory Toxicity:	0.62
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.907
Hematotoxicity:	0.317	Drug-induced Nephrotoxicity:	0.822
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.639	Hek293 Cytotoxicity:	0.162
BCF:	1.441 ? 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:	4.804 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.795 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.182 ? 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
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	stems	n.a.	n.a.	PMID[12932126]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20681570]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	Twigs and leaves	Taichung, Taiwan	1993-Aug	PMID[9322359]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5049	Garcinia multiflora	Species	Clusiaceae	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	1
Ratio	3

Activity Type	# Activity
Non-molecular	1
Others	3

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	14900.0	nM	PMID[20681570]
NPT2	Others	Unspecified	n.a.	Ratio	<=	3.0	n.a.	PMID[18955522]
NPT2	Others	Unspecified	n.a.	Ratio	>	3.0	n.a.	PMID[18955522]

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 NPC469856 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	7467
0.1-0.2	40427
0.2-0.3	1859
0.3-0.4	27
0.4-0.5	32
0.5-0.6	14
0.6-0.7	18
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8551	High Similarity	NPC46242
0.8551	High Similarity	NPC91887
0.8551	High Similarity	NPC93556
0.8493	Intermediate Similarity	NPC471970
0.8219	Intermediate Similarity	NPC469854
0.7973	Intermediate Similarity	NPC471971
0.7973	Intermediate Similarity	NPC471972
0.7973	Intermediate Similarity	NPC469855
0.7703	Intermediate Similarity	NPC469857
0.7703	Intermediate Similarity	NPC245760
0.76	Intermediate Similarity	NPC294330
0.7432	Intermediate Similarity	NPC297797
0.7324	Intermediate Similarity	NPC149773
0.6795	Remote Similarity	NPC30846
0.675	Remote Similarity	NPC237441
0.6625	Remote Similarity	NPC603871
0.6582	Remote Similarity	NPC165191
0.6582	Remote Similarity	NPC177501
0.65	Remote Similarity	NPC479151
0.6456	Remote Similarity	NPC114333
0.6456	Remote Similarity	NPC28592
0.6456	Remote Similarity	NPC51531
0.6375	Remote Similarity	NPC473479
0.6375	Remote Similarity	NPC50615
0.6375	Remote Similarity	NPC141650
0.6282	Remote Similarity	NPC289358
0.6282	Remote Similarity	NPC4289
0.6282	Remote Similarity	NPC42384
0.6173	Remote Similarity	NPC479148
0.6098	Remote Similarity	NPC482621
0.6071	Remote Similarity	NPC479146
0.5897	Remote Similarity	NPC473779
0.5833	Remote Similarity	NPC5014
0.5732	Remote Similarity	NPC473527
0.5714	Remote Similarity	NPC23667
0.5714	Remote Similarity	NPC157284
0.5682	Remote Similarity	NPC482617
0.5682	Remote Similarity	NPC482616
0.5658	Remote Similarity	NPC259400
0.5658	Remote Similarity	NPC130591
0.5658	Remote Similarity	NPC234637
0.5568	Remote Similarity	NPC482618
0.5513	Remote Similarity	NPC611064
0.5357	Remote Similarity	NPC198803
0.5059	Remote Similarity	NPC479147

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469856 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3779
0.1-0.2	5331
0.2-0.3	40
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