NPASS Compound

Natural Product: NPC321301

Natural Product ID	NPC321301
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FFRSMYORIKCGHG-SHUBQVNDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
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 81 84 0 0 0 0 0 0 0 0999 V2000 8.4433 1.5161 -0.7447 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1308 0.1004 -0.2444 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0326 -0.8295 -1.0281 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7174 -0.2387 -0.5762 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4437 -1.1873 -1.2826 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5774 0.5928 -0.0404 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2952 0.0163 -0.5347 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0496 0.7454 -0.0465 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8500 0.0353 -0.6343 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9683 -1.4161 -0.1116 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5860 -1.8360 0.3160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2851 -0.8051 -0.2677 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4955 -1.0352 -1.7407 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5694 -0.5996 0.4283 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0360 -1.3371 1.4031 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3725 -0.9495 1.9728 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2510 -0.6616 0.7536 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7012 -0.7531 1.0751 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0188 -2.2401 1.2906 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1221 -0.0364 2.3155 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4857 -0.3384 -0.1475 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6184 -0.3717 -1.4005 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4814 0.6036 -1.3173 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8363 0.5904 0.0579 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1788 1.8481 0.7795 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3405 0.5460 -0.0666 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6635 1.5314 -0.6208 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1753 1.5625 -0.7783 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5297 0.4823 -0.0520 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6229 0.8225 1.3966 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5415 -1.2446 -0.4050 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4195 -2.1718 -1.1900 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1846 2.1516 -0.3980 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5409 2.6628 -1.3332 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0412 2.9742 0.3079 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2027 2.2617 0.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7396 1.6978 -1.5940 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4836 1.5772 -1.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3010 -0.0180 0.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9639 -1.8742 -0.7200 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0658 -0.4060 -0.9541 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7519 -0.6832 -2.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7427 1.6581 -0.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6466 0.5566 1.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2457 0.1218 -1.6578 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2633 -1.0589 -0.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0826 0.5868 1.0772 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9086 0.0968 -1.7165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6385 -1.4718 0.7733 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5234 -1.8612 1.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4110 -2.8399 -0.1313 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2373 -2.1041 -1.9525 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6006 -0.9662 -1.9503 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0364 -0.3428 -2.3916 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4606 -2.1726 1.7520 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2713 -0.0648 2.6145 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8316 -1.8146 2.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0219 -1.5109 0.0434 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3804 -2.8801 0.6832 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0774 -2.4641 1.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8569 -2.5218 2.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6037 -0.7186 3.0770 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3242 0.4836 2.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9648 0.6566 2.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9798 0.6481 -0.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2873 -0.0958 -2.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3050 -1.4197 -1.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7389 0.3306 -2.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8455 1.6202 -1.5895 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5493 1.9914 1.6732 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2578 1.9802 0.9765 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9069 2.7006 0.0897 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2109 2.3941 -0.9973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0801 1.6617 -1.8548 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1105 2.5383 -0.2727 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3946 0.7922 1.8631 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9552 1.8774 1.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2442 0.1220 1.9861 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3195 -0.7846 -0.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9051 -2.9783 -0.8668 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8635 3.9686 0.3917 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 1 21 31 1 0 10 32 1 0 8 33 1 0 33 34 2 0 33 35 1 0 29 9 1 0 29 12 1 0 26 14 1 0 24 17 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 0 3 40 1 0 3 41 1 0 3 42 1 0 6 43 1 0 6 44 1 0 7 45 1 0 7 46 1 0 8 47 1 1 9 48 1 6 10 49 1 1 11 50 1 0 11 51 1 0 13 52 1 0 13 53 1 0 13 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 6 19 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 20 64 1 0 21 65 1 1 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 32 80 1 0 35 81 1 0 M END

Standard InCHIKey	FFRSMYORIKCGHG-SHUBQVNDSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-17(2)21(31)10-8-18(26(34)35)25-22(32)16-30(7)20-9-11-23-27(3,4)24(33)13-14-28(23,5)19(20)12-15-29(25,30)6/h9,12,17-18,22-25,32-33H,8,10-11,13-16H2,1-7H3,(H,34,35)/t18-,22-,23+,24-,25+,28-,29-,30+/m1/s1
SMILES	CC(C)C(=O)CC[C@H]([C@H]1[C@@H](C[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)C3=CC[C@]12C)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	526.615 ? Van der Waals volume.
Dense:	0.924	LogP:	3.055 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.728 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.284 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	22.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.458	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.059	Fsp³:	0.8
MCE-18:	84.37 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.775	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.065 ? 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:	0.327	Promiscuous compounds:	0.129

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.438	MDCK Permeability:	-4.946
Pgp-inhibitor:	0.002	Pgp-substrate:	0.077
PAMPA:	0.998 ? 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%):	0.006	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.743

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.999
Plasma Protein Binding (PPB):	85.08%	Volume Distribution (VD):	-0.233
Fu:	15.468% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.004
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.989	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.549
HLM stability:	0.005 ? 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):

5.555

Half-life (T1/2):

0.877

ADMET: Toxicity

hERG Blockers:	0.038	hERG Blockers (10um):	0.109
Human Hepatotoxicity (H-HT):	0.531	Drug-induced Liver Injury (DILI):	0.222
AMES Toxicity:	0.245	Rat Oral Acute Toxicity:	0.368
Maximum Recommended Daily Dose:	0.283	Skin Sensitization:	0.935
Carcinogencity:	0.503	Eye Corrosion:	0.004
Eye Irritation:	0.234	Respiratory Toxicity:	0.649
Drug-induced Neurotoxicity:	0.103	Ototoxicity:	0.73
Hematotoxicity:	0.425	Drug-induced Nephrotoxicity:	0.867
Genotoxicity:	0.698	RPMI-8226 Immunitoxicity:	0.096
A549 Cytotoxicity:	0.119	Hek293 Cytotoxicity:	0.179
BCF:	0.557 ? 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:	3.342 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.934 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.22 ? 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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	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	4

Activity Type	# Activity
Cell line	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
NPT111	Cell line	K562	Homo sapiens	IC50	>	40000.0	nM	PMID[27808511]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[27808511]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	>	40000.0	nM	PMID[27808511]
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	>	40000.0	nM	PMID[27808511]

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 NPC321301 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	15779
0.1-0.2	29049
0.2-0.3	4610
0.3-0.4	329
0.4-0.5	51
0.5-0.6	19
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC484975
0.7937	Intermediate Similarity	NPC222845
0.7937	Intermediate Similarity	NPC296577
0.7692	Intermediate Similarity	NPC45324
0.7692	Intermediate Similarity	NPC162001
0.7576	Intermediate Similarity	NPC186810
0.7576	Intermediate Similarity	NPC48647
0.6479	Remote Similarity	NPC484967
0.6429	Remote Similarity	NPC66429
0.6301	Remote Similarity	NPC263347
0.625	Remote Similarity	NPC152897
0.625	Remote Similarity	NPC484968
0.6216	Remote Similarity	NPC484969
0.6164	Remote Similarity	NPC155676
0.6	Remote Similarity	NPC288464
0.6	Remote Similarity	NPC477813
0.6	Remote Similarity	NPC607198
0.5915	Remote Similarity	NPC84271
0.5915	Remote Similarity	NPC102414
0.5753	Remote Similarity	NPC77168
0.5733	Remote Similarity	NPC141401
0.5676	Remote Similarity	NPC469406
0.5676	Remote Similarity	NPC477812
0.5541	Remote Similarity	NPC484976
0.5467	Remote Similarity	NPC214697
0.5405	Remote Similarity	NPC212948
0.5395	Remote Similarity	NPC123854
0.5333	Remote Similarity	NPC203035
0.5325	Remote Similarity	NPC7165
0.527	Remote Similarity	NPC76895
0.5139	Remote Similarity	NPC231310
0.5132	Remote Similarity	NPC484971
0.5132	Remote Similarity	NPC484970
0.5125	Remote Similarity	NPC469432
0.5067	Remote Similarity	NPC247406
0.5063	Remote Similarity	NPC489791

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC321301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5296
0.1-0.2	3729
0.2-0.3	124
0.3-0.4	1
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