NPASS Compound

Natural Product: NPC149773

Natural Product ID	NPC149773
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Aristophenone A
IUPAC Name	n.a.
Synonyms	Aristophenone A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL516196
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 81 83 0 0 0 0 0 0 0 0999 V2000 0.8264 4.2944 -1.5955 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6230 3.9650 -1.5267 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1604 3.2906 -0.5172 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3421 2.8326 0.5879 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3928 1.3484 0.8903 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7527 0.8728 1.2562 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9717 -0.5541 1.1279 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2634 -0.7630 0.2938 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4112 -0.1148 0.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1691 0.7396 0.3669 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9994 1.1632 -1.0397 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3153 1.3677 1.1186 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9487 -1.4920 0.6075 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2331 -0.8838 -0.0373 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0042 0.5841 -0.3052 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0936 1.1362 -1.3538 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3310 -0.8762 1.0046 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9370 -1.9847 1.1942 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6596 0.3167 1.7394 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6267 1.1441 1.9858 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4557 1.8112 3.1732 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9243 0.6123 2.3152 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8988 1.6308 3.1537 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2156 -0.0029 2.1421 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2261 0.2655 3.0777 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5059 -0.2213 2.9417 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8569 -1.0040 1.8667 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9018 -1.2796 0.9441 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5986 -0.7821 1.0833 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2040 -2.0629 -0.1562 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1441 -1.4903 1.7381 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8587 -1.5448 -1.2123 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0746 -1.7651 -2.3964 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0676 -2.8562 -3.1193 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8992 -4.0145 -2.7832 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8083 -2.9711 -4.3502 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5742 -2.6161 -0.2241 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4575 -2.2868 1.8457 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4837 4.4400 -2.6753 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4765 3.4272 -1.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1069 4.8621 -0.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0239 5.0253 -2.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2203 3.0988 -0.5473 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6388 3.3915 1.5252 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7282 3.0959 0.4260 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0084 1.2072 2.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4741 1.4321 0.5693 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3355 -0.9207 2.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4651 -1.8308 0.3114 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1647 -0.3150 -0.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5952 -0.3791 2.0077 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6295 2.0452 -1.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9620 1.4740 -1.2486 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1935 0.3104 -1.7243 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2930 1.1326 2.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3454 2.4537 0.9959 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2411 0.9699 0.6427 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7222 1.4481 4.0679 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9591 0.8769 3.9259 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2605 0.0099 3.6928 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9265 -0.9990 0.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9626 -1.8901 -0.7772 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8439 -1.2602 2.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4147 -2.4296 -0.8231 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7147 -0.8496 -1.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5817 -0.9658 -2.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9776 -4.1436 -1.7020 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9278 -3.9250 -3.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4708 -4.9277 -3.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5357 -3.7590 -4.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2325 -1.9655 -4.5379 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1432 -3.1781 -5.2262 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1942 -3.2749 0.4646 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0911 -2.2806 -1.1100 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7017 -3.3100 -0.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0217 -3.2229 1.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -1.6410 2.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4206 -2.5411 2.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8395 4.7801 -3.5071 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1875 5.2102 -2.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9979 3.5090 -3.0553 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 1 0 7 8 1 0 8 9 1 0 9 10 2 3 10 11 1 0 10 12 1 0 7 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 14 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 19 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 14 32 1 6 32 33 1 0 33 34 2 3 34 35 1 0 34 36 1 0 13 37 1 0 13 38 1 0 2 39 1 0 20 5 1 0 29 24 1 0 15 5 1 0 1 40 1 0 1 41 1 0 1 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 6 46 1 0 6 47 1 0 7 48 1 1 8 49 1 0 8 50 1 0 9 51 1 0 11 52 1 0 11 53 1 0 11 54 1 0 12 55 1 0 12 56 1 0 12 57 1 0 21 58 1 0 25 59 1 0 26 60 1 0 29 61 1 0 30 62 1 0 31 63 1 0 32 64 1 0 32 65 1 0 33 66 1 0 35 67 1 0 35 68 1 0 35 69 1 0 36 70 1 0 36 71 1 0 36 72 1 0 37 73 1 0 37 74 1 0 37 75 1 0 38 76 1 0 38 77 1 0 38 78 1 0 39 79 1 0 39 80 1 0 39 81 1 0 M END

Standard InCHIKey	ZWAKZDYMQXZEGP-UMJMCJBLSA-N
Standard InCHI	InChI=1S/C33H42O6/c1-19(2)9-11-23-18-32(15-13-20(3)4)28(37)26(27(36)22-10-12-24(34)25(35)17-22)29(38)33(30(32)39,31(23,7)8)16-14-21(5)6/h9-10,12-14,17,23,34-35,37H,11,15-16,18H2,1-8H3/t23-,32+,33-/m1/s1
SMILES	CC(=CC[C@]12C[C@@H](CC=C(C)C)C([C@@](C2=O)(C(=O)C(=C1O)C(=O)c1ccc(c(c1)O)O)CC=C(C)C)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.3	Volume:	580.031 ? Van der Waals volume.
Dense:	0.921	LogP:	5.455 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.382 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.32 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	22.0
TPSA:	111.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.106	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.23	Fsp³:	0.485
MCE-18:	96.122 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.972	Fluc inhibitor:	0.126 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.066 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.509 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.605	Promiscuous compounds:	0.226

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.799	MDCK Permeability:	-4.684
Pgp-inhibitor:	0.0	Pgp-substrate:	0.004
PAMPA:	0.996 ? 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%):	0.031	30% Bioavailability (F30%):	0.003
50% Bioavailability (F50%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.954
Plasma Protein Binding (PPB):	83.928%	Volume Distribution (VD):	0.13
Fu:	20.845% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.978
OATP1B3 inhibitor:	0.249	BCRP inhibitor:	0.001
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.147
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.427	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.644
HLM stability:	1.0 ? 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):

6.979

Half-life (T1/2):

1.254

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.163
Human Hepatotoxicity (H-HT):	0.701	Drug-induced Liver Injury (DILI):	0.747
AMES Toxicity:	0.627	Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.25	Skin Sensitization:	0.997
Carcinogencity:	0.599	Eye Corrosion:	0.0
Eye Irritation:	0.074	Respiratory Toxicity:	0.754
Drug-induced Neurotoxicity:	0.031	Ototoxicity:	0.879
Hematotoxicity:	0.642	Drug-induced Nephrotoxicity:	0.957
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.742	Hek293 Cytotoxicity:	0.187
BCF:	1.686 ? 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:	5.35 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.39 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.08 ? 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]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14600386]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[15787435]
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]
NPO21424	Garcinia xanthochymus	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]
NPO21424	Garcinia xanthochymus	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]
NPO21424	Garcinia xanthochymus	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]
NPO21424	Garcinia xanthochymus	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	5
Ratio	3

Activity Type	# Activity
Cell line	4
Others	4

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
NPT660	Cell line	SW480	Homo sapiens	IC50	=	33300.0	nM	PMID[17190448]
NPT515	Cell line	SGC-7901	Homo sapiens	IC50	=	13.71	ug.mL-1	PMID[32791400]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	13.71	ug.mL-1	PMID[32791400]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	9.22	ug.mL-1	PMID[32791400]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	125000.0	nM	PMID[20014752]
NPT2	Others	Unspecified	n.a.	Ratio	<=	3.0	n.a.	PubChem BioAssay data set

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 NPC149773 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	6634
0.1-0.2	40833
0.2-0.3	2250
0.3-0.4	57
0.4-0.5	13
0.5-0.6	24
0.6-0.7	15
0.7-0.8	0
0.8-0.85	9
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC165191
0.875	High Similarity	NPC30846
0.875	High Similarity	NPC177501
0.8594	High Similarity	NPC114333
0.8594	High Similarity	NPC28592
0.8594	High Similarity	NPC51531
0.8571	High Similarity	NPC46242
0.8571	High Similarity	NPC91887
0.8571	High Similarity	NPC93556
0.8462	Intermediate Similarity	NPC473479
0.8462	Intermediate Similarity	NPC50615
0.8462	Intermediate Similarity	NPC141650
0.8438	Intermediate Similarity	NPC297797
0.8182	Intermediate Similarity	NPC469857
0.8182	Intermediate Similarity	NPC245760
0.8125	Intermediate Similarity	NPC289358
0.8125	Intermediate Similarity	NPC4289
0.8125	Intermediate Similarity	NPC42384
0.7941	Intermediate Similarity	NPC471971
0.7941	Intermediate Similarity	NPC471972
0.7941	Intermediate Similarity	NPC469855
0.7705	Intermediate Similarity	NPC259400
0.7705	Intermediate Similarity	NPC130591
0.7705	Intermediate Similarity	NPC234637
0.7429	Intermediate Similarity	NPC5014
0.7324	Intermediate Similarity	NPC469856
0.7286	Intermediate Similarity	NPC23667
0.7286	Intermediate Similarity	NPC157284
0.7286	Intermediate Similarity	NPC294330
0.7222	Intermediate Similarity	NPC471970
0.7183	Intermediate Similarity	NPC469854
0.6944	Remote Similarity	NPC603871
0.6923	Remote Similarity	NPC611064
0.6901	Remote Similarity	NPC479148
0.6857	Remote Similarity	NPC198803
0.6849	Remote Similarity	NPC237441
0.6806	Remote Similarity	NPC482621
0.6806	Remote Similarity	NPC479151
0.68	Remote Similarity	NPC482618
0.6711	Remote Similarity	NPC482617
0.6711	Remote Similarity	NPC482616
0.6618	Remote Similarity	NPC473779
0.6184	Remote Similarity	NPC25736
0.6164	Remote Similarity	NPC48949
0.6164	Remote Similarity	NPC473527
0.6104	Remote Similarity	NPC479146
0.5844	Remote Similarity	NPC482619
0.5738	Remote Similarity	NPC602123
0.5584	Remote Similarity	NPC8493
0.5584	Remote Similarity	NPC469375
0.5584	Remote Similarity	NPC110855
0.5584	Remote Similarity	NPC144247
0.5556	Remote Similarity	NPC600619
0.5432	Remote Similarity	NPC231479
0.5375	Remote Similarity	NPC264229
0.5375	Remote Similarity	NPC46549
0.5375	Remote Similarity	NPC606601
0.5342	Remote Similarity	NPC474715
0.5333	Remote Similarity	NPC600618
0.5309	Remote Similarity	NPC294679
0.5309	Remote Similarity	NPC145301
0.5309	Remote Similarity	NPC302044
0.5309	Remote Similarity	NPC600911
0.5211	Remote Similarity	NPC471481
0.5211	Remote Similarity	NPC610194
0.5195	Remote Similarity	NPC479147
0.5185	Remote Similarity	NPC7464
0.5176	Remote Similarity	NPC482620
0.5122	Remote Similarity	NPC606237
0.5077	Remote Similarity	NPC605738

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC149773 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3153
0.1-0.2	5918
0.2-0.3	79
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