NPASS Compound

Natural Product: NPC601194

Natural Product ID	NPC601194
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZNDCXCGTAALLTP-DKYKKQJNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2203597
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 80 83 0 0 0 0 0 0 0 0999 V2000 4.6204 2.0913 1.3957 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7260 1.9897 0.4207 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5719 1.3001 -0.6927 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2903 0.5922 -1.0281 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5066 -0.8787 -1.1797 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3367 -1.6611 -1.5201 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8875 -3.1522 -1.6751 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1485 -1.8496 -0.7352 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2235 -2.4745 0.6230 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7275 -2.5543 0.9886 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0333 -1.8715 -0.1139 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3684 -2.8543 -1.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1682 -1.0483 0.3122 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3944 0.1154 -0.2799 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5885 0.6810 -1.3635 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6701 -0.0548 -1.6885 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0833 -0.8647 -0.5289 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1786 0.0144 0.6978 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5574 0.8978 0.2188 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1152 1.4715 1.5536 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8128 2.0829 -0.6814 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1606 2.7187 -0.3355 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2008 1.6625 -0.6686 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4830 2.1853 -0.7339 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0660 0.5656 0.3404 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5399 0.9930 1.7107 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0415 -0.5409 -0.0967 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7122 -0.0329 0.3148 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4621 -0.9612 1.4887 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0672 -1.4923 1.3706 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7091 -2.3344 2.2214 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0057 2.6691 0.7082 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9520 2.5912 -0.1083 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1895 3.3959 1.8655 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0108 2.4870 2.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 1.0543 1.5726 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8188 2.7581 1.0688 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4074 1.2552 -1.3732 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4892 0.8984 -0.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0018 1.0486 -2.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1359 -1.2976 -0.3462 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2403 -0.9693 -2.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0383 -1.4518 -2.5860 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0553 -3.8089 -1.9171 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2814 -3.3633 -0.6632 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7132 -3.1507 -2.3811 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5927 -2.7036 -1.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5851 -3.5322 0.5061 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7980 -1.9523 1.3757 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4006 -3.6119 1.0554 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5660 -2.1031 1.9903 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4944 -2.9931 -1.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0031 -3.8925 -0.9789 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2156 -2.5171 -2.2147 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2616 0.7558 -2.2674 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3015 1.7451 -1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5166 0.6445 -1.9181 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5113 -0.6262 -2.6249 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3453 -0.1025 1.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1258 1.0989 0.3838 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0866 -0.0812 1.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0536 1.8446 1.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6875 2.3701 1.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1037 0.7528 2.3699 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9008 1.8099 -1.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0472 2.8555 -0.4780 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2071 3.0675 0.6934 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3113 3.5993 -0.9915 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8909 1.2342 -1.6586 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8341 2.2389 -1.6636 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6186 0.1132 2.3764 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6077 1.3332 1.5631 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0060 1.8435 2.1281 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5696 -1.0171 -0.9792 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0612 -1.3014 0.7121 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0323 -0.1155 -0.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6640 -0.7025 -0.5958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6844 -0.5239 2.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1344 -1.8334 1.3494 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0968 3.4507 2.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 14 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 2 32 1 0 32 33 2 0 32 34 1 0 17 8 1 0 28 19 1 0 17 11 1 0 30 13 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 6 7 44 1 0 7 45 1 0 7 46 1 0 8 47 1 6 9 48 1 0 9 49 1 0 10 50 1 0 10 51 1 0 12 52 1 0 12 53 1 0 12 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 18 59 1 0 18 60 1 0 18 61 1 0 20 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 23 69 1 6 24 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 27 76 1 0 28 77 1 6 29 78 1 0 29 79 1 0 34 80 1 0 M END

Standard InCHIKey	ZNDCXCGTAALLTP-DKYKKQJNSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-18(9-8-10-19(2)26(33)34)20-11-16-30(7)25-21(12-15-29(20,30)6)28(5)14-13-24(32)27(3,4)23(28)17-22(25)31/h10,18,20,23-24,32H,8-9,11-17H2,1-7H3,(H,33,34)/b19-10+/t18-,20-,23+,24+,28-,29-,30+/m1/s1
SMILES	C/C(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3=O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	517.825 ? Van der Waals volume.
Dense:	0.908	LogP:	4.121 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.46 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.316 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.437	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.751	Fsp³:	0.8
MCE-18:	83.111 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.8	Fluc inhibitor:	0.002 ? 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:	0.442	Promiscuous compounds:	0.296

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.328	MDCK Permeability:	-4.944
Pgp-inhibitor:	0.108	Pgp-substrate:	0.006
PAMPA:	0.992 ? 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):	0.009
20% Bioavailability (F20%):	0.867	30% Bioavailability (F30%):	0.708
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.971
Plasma Protein Binding (PPB):	88.309%	Volume Distribution (VD):	-0.521
Fu:	10.333% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.052
BSEP inhibitor:	0.831

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.924	CYP2C19-substrate:	0.197
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.898	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.325
HLM stability:	0.743 ? 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):

6.125

Half-life (T1/2):

0.665

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.026
Human Hepatotoxicity (H-HT):	0.784	Drug-induced Liver Injury (DILI):	0.435
AMES Toxicity:	0.258	Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.46	Skin Sensitization:	0.996
Carcinogencity:	0.632	Eye Corrosion:	0.112
Eye Irritation:	0.912	Respiratory Toxicity:	0.918
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.702
Hematotoxicity:	0.626	Drug-induced Nephrotoxicity:	0.933
Genotoxicity:	0.558	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.123	Hek293 Cytotoxicity:	0.144
BCF:	0.868 ? 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:	4.049 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.645 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.831 ? 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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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	2

Activity Type	# Activity
Individual protein	1
Cell line	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT253	Individual protein	HMG-CoA reductase	Homo sapiens	IC50	=	22300.0	nM	PMID[26287401]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	300000.0	nM	PMID[23092389]
NPT65	Cell line	HepG2	Homo sapiens	Activity	=	24.27	U/L	PMID[29353722]
NPT65	Cell line	HepG2	Homo sapiens	Activity	=	20.95	U/L	PMID[29353722]

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 NPC601194 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	17506
0.1-0.2	26714
0.2-0.3	4914
0.3-0.4	531
0.4-0.5	131
0.5-0.6	38
0.6-0.7	11
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	Natural Product ID
0.7742	Intermediate Similarity	NPC275740
0.7742	Intermediate Similarity	NPC86319
0.7656	Intermediate Similarity	NPC69454
0.7391	Intermediate Similarity	NPC489808
0.7391	Intermediate Similarity	NPC489800
0.7273	Intermediate Similarity	NPC8571
0.7031	Intermediate Similarity	NPC110021
0.7031	Intermediate Similarity	NPC482426
0.6923	Remote Similarity	NPC482424
0.6818	Remote Similarity	NPC259286
0.6818	Remote Similarity	NPC83216
0.6818	Remote Similarity	NPC484085
0.6769	Remote Similarity	NPC482423
0.6716	Remote Similarity	NPC183283
0.6338	Remote Similarity	NPC482518
0.629	Remote Similarity	NPC482425
0.6286	Remote Similarity	NPC212948
0.6173	Remote Similarity	NPC202051
0.6104	Remote Similarity	NPC489799
0.5972	Remote Similarity	NPC472240
0.5972	Remote Similarity	NPC262858
0.5946	Remote Similarity	NPC489798
0.5946	Remote Similarity	NPC489801
0.5915	Remote Similarity	NPC162703
0.5844	Remote Similarity	NPC478302
0.5811	Remote Similarity	NPC456
0.5811	Remote Similarity	NPC472941
0.5811	Remote Similarity	NPC202814
0.5789	Remote Similarity	NPC293753
0.5775	Remote Similarity	NPC142253
0.5775	Remote Similarity	NPC3511
0.5753	Remote Similarity	NPC484971
0.5753	Remote Similarity	NPC484970
0.5733	Remote Similarity	NPC482515
0.5733	Remote Similarity	NPC482517
0.5584	Remote Similarity	NPC489807
0.5584	Remote Similarity	NPC478297
0.5584	Remote Similarity	NPC478298
0.5556	Remote Similarity	NPC41539
0.5493	Remote Similarity	NPC249954
0.5479	Remote Similarity	NPC191684
0.5455	Remote Similarity	NPC489789
0.5441	Remote Similarity	NPC46160
0.5441	Remote Similarity	NPC202642
0.5429	Remote Similarity	NPC110923
0.5429	Remote Similarity	NPC74296
0.5405	Remote Similarity	NPC482597
0.5342	Remote Similarity	NPC472940
0.5333	Remote Similarity	NPC138536
0.5316	Remote Similarity	NPC472924
0.5278	Remote Similarity	NPC99909
0.5211	Remote Similarity	NPC131470
0.519	Remote Similarity	NPC39082
0.519	Remote Similarity	NPC610107
0.5185	Remote Similarity	NPC482571
0.5139	Remote Similarity	NPC90965
0.5068	Remote Similarity	NPC605549

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC601194 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5800
0.1-0.2	3175
0.2-0.3	170
0.3-0.4	5
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